Here’s a fave from 2023 on how to procrastinate better.

Not that you would EVER, in a million years, be reading this post instead of sending that important sales email…😉

How To Turn Procrastination Into Your Superpower

(Original publication date: July 11, 2023)

Hi, my name is Kathryn and I procrastinate.

Hopefully, right now, you’re thinking, No way. You deliver the O’Daily to my inbox every week on time.

But you also might be thinking, This does seem thrown together so that checks out. 😂😳

I used to hate my procrastination. I would be insanely jealous of my college friends who would be done with papers on TUESDAY for a Friday deadline. 🤯🤯🤯

I would sit down at my laptop on Tuesday night, committed to getting it done.

Four hours of Facebook later (it was still cool, okay?), I would head to bed with barely an outline.

Then I read this amazing essay by John Perry on “Structured Procrastination” that changed everything.

tl;dr — expect your procrastination. use it to your advantage.

How Structured Procrastination Works

1. Make a list of tasks in priority order

2. Do everything else on the list to avoid #1

3. Behold your amazing productivity and empty to-do list (except for 1 item)!

But…you didn’t get #1 done?!?

No problem.

1. Find an item that’s MORE important than #1

2. Tackle item-formerly-known-as-#1 to avoid doing new item #1

3. Congratulations! Your procrastination is helping you get shit done!

3 Ways To Activate “Structured Procrastination”

1. Create deadlines.

Schedule a meeting, tell someone you will have it by a certain date, hire a coach, make an accountability pod, sign up for a pitch competition, whatever will feel “real” and create pressure on your to-do list.

2. Leverage your “Tendency.”

I am an Upholder/Obliger. So I *KNOW* that I keep my commitments to others. When something is important, I promise someone I will do it.

3. Use calendar blocks (to know you’re behind).

I use calendar blocks to help me visualize the actual time I have to complete a task or project. A Thursday deadline becomes urgent on Monday when I clearly see I’m booked with meetings on Tuesday and Wednesday.

Procrastination and Long-Term Goals

You might be asking, but Kathryn, how could you train for Ironmans as a procrastinator???

Or maybe you’re thinking, how the hell can I build a big ass company — a 10 year endeavor — when I procrastinate??

Here’s what’s worked for me — set up systems that make it easy to do the right thing.

I didn’t think of Ironman training as “I’m going to do this really hard thing today and then repeat it every day until forever.”

I met my friends for a bike ride. I went to Masters Swim practice. I did what my coach wrote in the training plan.

A lot of it was “show up” and then let habit (and peer pressure!) carry you.

Same can be true for startups and company-building.

Here are common accountability mechanisms:

• customer meetings/deliverables

• investor updates

• board meetings

• quarterly (monthly, weekly, daily) sales targets

• weekly team meetings

• daily standups

• product roadmaps/releases

• internal meetings about high priority projects

Some of these naturally occur, some will be cultivated as you grow, and some you may want to add intentionally today!

Trust Your Procrastination

I’m such a sophisticated procrastinator that I keep a 3 item to-do list.

Let me explain.

I never put “clean the car” on my to-do list.

I know myself well enough to trust that I will suddenly, urgently need to vacuum the car 15 minutes before we leave for a road trip.

Don’t force that gnarly chore on a laid back family weekend.

Same with wiping down ceiling fans, cleaning out photos, updating old blog posts, and whatever other crappy task I *should* do but just can’t make myself at the moment.

Enjoy the Guilt

All the anti-procrastinators right now:

But Kathryn — it feels so good to get your stuff done instead of having it hang over you!

Allow me to offer a different perspective.

I like the guilt.

When you read a blog when you *should* be replying to emails, it’s so much more indulgent and enjoyable!

I’m going to treat myself. I stole this time! How luxurious to read the O’Daily.

If I’m already at Inbox Zero, I tend to meander aimlessly around Slack or LinkedIn. No productive learning or stolen moments of fun.

LAME.

It reminds me of the meeting cancelation paradox:

• Have 30 minutes open on your calendar? → That’s nice.

• Someone cancels a 30 minute meeting? → OMG WHAT WILL I DO WITH ALL THIS EXTRA TIME??

Instead of guilt, embrace the joy of procrastinating!

Repeat after me:

• “I work well to deadline.”

• “I know I’ll get it done when it matters.”

• “I love using my procrastination to be productive and have fun.”

• “I don’t beat myself up for procrastinating, I revel in it!”

Procrastination: Another Way to Say No

I spend a lot of time (practicing how to get better at) saying no:

• why to say no

• 7 ways to say no

• 4 more ways to say no

• how to say no to your boss

• how to have fewer meetings

• how to prioritize (aka figure out when to say no)

Procrastination is a secret, subconscious way to say no.

You say no when you have to. Because you ran out of time to do only the most important things!

It’s also a great way to say no to perfectionism and yes to shipping!

You may want 20 hours to perfect your slide deck but if you only have 2 hours, you figure out a way.

It’s not perfect but it’s live in the world which is 100x more important than perfect, especially at startups!

My 3 Steps Forcing Functions To Blog Every Week

So how the heck to I get my blog out every week?

STEP 1: I tell my wonderful readers that I will email them on Tues. They are counting on me!!! (My Obliger tendency believes this. Reality is irrelevant. 😂)

STEP 2: I schedule a calendar block and stick to it — no meeting creep!

STEP 3: **where the magic happens** I include time in my calendar block for Inbox Zero and other random productive tasks to make the most of my structured procrastination!

What tips or strategies do you use to avoid or leverage your procrastination??

(Psst…4th of July is this Saturday if you have been in an AI chat vortex!)

Ain’t nobody got time for a wordy blog post.

But everyone has time to scroll throwback startup photos!

In no particular order, here’s some favorite and hilarious moments :)

Holla if you remember any of these!

Got some favorite photos? What are your best startup memories?

AWESOME!!

The world needs more angel investors.

(They are called angels for a reason! 😇)

Angel investors are a critical part of every healthy startup ecosystem and help SO many founders in the early days.

They provide:

• Early working capital

• A vote of confidence! Belief in the founder and what they are building

• Helpful customer intros or other industry expertise

• Social proof for other investors or customers

I often talk to successful business people or high net worth individuals who are interested in angel investing but aren’t sure where or how to begin.

Here are some questions I like to ask to help someone get clear on their strategy!

1. Why do you want to angel invest?

No wrong answer except, “I don’t know.”

Your “why” will determine everything else about your angel investing!

Some common answers I hear:

• I want to help founders (especially founders like me).

• I want to diversify my portfolio and test a new investment class.

• I want to get more involved in the startup ecosystem.

• I’ve had a great career and want to pay it forward.

• A lead gen and/or research tool — it’s part of my company’s business strategy (often with agencies or entrepreneur-owned businesses that may partner or acquire you).

• I’m interested in it and want to try it out.

Usually people will say they want to do it for #allthereasons!

That’s great and there’s always many levels of benefit, but I’d get super clear on the *TOP* priority.

Because each “why” leads to a slightly different approach and criteria of success!

2. What do you think makes a great founder?

Again, no wrong answer but it’s important to identify ahead of time what you think matters.

• Do you want someone scrappy? Salesy? Brainy? Rough around the edges? Polished?

• Do you like a certain background? Someone from your hometown? Former athlete? F500 experience? Skipped college?

• Are there types of people you want to specifically invest in (e.g. recent grads, women, doctors turned entrepreneurs, immigrants or first-gen Americans, etc)?

A lot of this will be influenced by your own experience in the world!

You’ll adjust what you look for over time as you gain information and data points but it’s good to have a starting hypothesis.

3. How do you want to add value? What is your expertise?

You may say, I just want to write a check.

You may say, I have 20 years building software so I want to mentor a technical founder and help with engineering strategy.

Both are correct answers.

Both result in different angel investing experiences and strategies!

Do some self-reflection on where you can be helpful and how much help you want to offer.

That will influence where and how you deploy your angel checks!

Speaking of checks…

4. What is your financial framework and timeline?

Before you make it rain, make a plan!

Like with all experiments, it’s better to decide your protocol ahead of time than on the fly in a founder meeting.

It’s hard to think rationally when a charismatic founder is explaining how they’re going change the world and you’re ready to send a wire on the spot for $1M!

(All the founders are like, yes, Kathryn, they should do that 😉)

Here’s some example deployment strategies:

• I’m going to write 10-20 checks of $25,000 over the next 2 years.

• I’m going to write 3 checks of $10,000 and then see how I feel.

• I’m going to write 5 checks of $50,000 as I find companies I love and can help.

Get clear on:

• How much money total

• How many investments

• Ideal/average check size

• Over what timeframe

• When you will evaluate and assess

5. What are you passionate about?

Here’s where it gets fun:

• What do you really, really care about?

• What do you believe in?

• What do you want to put your hard earned money and time and energy behind?

• What do you want the future to look like?

Maybe you’ve already identified it in the previous questions.

If not, think about it now!

This is also a catch-all for things like:

• Do you want to invest in certain industries? Business types? Geographies?

• Anything that is a hard no for you? (e.g. gambling, fossil fuels or maybe you love those things 😜)

• Any other considerations or guardrails that you want to identify upfront?

Usually after someone gets clear on what and how they want to invest, the next question is:

“How do I get started???”

But that’s a whole new topic 😉 (Let me know if you want a follow up post!)

The most important thing is to go in with a plan…and be open to the plan changing.

Because, just like with startups, you will learn and iterate along the way!

What advice do you have for folks thinking about angel investing? What helped you get started? What things did you learn the hard way? 😉

(Hi, Dad, if you’re reading this 👋)

I learned many, many things from my dad about business (and life!).

Values like:

• Integrity

• Work ethic

• Discipline

Habits like:

• Taking a 15 minute couch (or floor) nap for maximum productivity

• Be home for family dinner and don’t talk about work!

• Work with people you like and trust

A few of the most important lessons didn’t look business-y at all.

Small moments that made a big impact.

Here are 4 moments that have stuck with me for decades.

To my dad — and all the dads — thanks for empowering your children. Especially the daughters.

We’re all stronger and more resilient because our dads spent time with us.

(To my mom and all the moms — ditto but that’s a separate post! 😉)

1. “If they crowd the plate, throw inside.”

I was a fastpitch softball pitcher for 10+ years with my dad as #1 practice buddy and forever catcher.

At the end of a practice session, I’d pitch to pretend batters. He’d call pitches and we’d talk about strategy.

When I first started, I was afraid of hitting batters. If someone stood close to the plate, I’d adjust my pitches to accommodate them.

WRONG!

“If they crowd the plate, throw inside.”

My dad quickly taught me:

• You own the plate.

• If someone gets too close, throw a hard inside pitch. No change ups!

• If it hits them, it hits them. No big deal. Now they know.

• This is part of the game.

Small moment, big lesson:

• You’re in charge.

• Claim your space.

• “Mistakes” (hitting someone) are okay. Make a mistake in a positive direction.

• Don’t take on someone else’s problem.

Playing hard and smart is a part of the game!

2. “If you’re going to foul, make it count.”

Basketball, another favorite sport played with my dad.

Yes, he taught me lots of basketball skills. Defensive footwork, layups, jump shots, post moves.

The most memorable?

“If you’re going to foul, make it count.”

If you’re going to make physical contact when playing defense, make sure it’s hard, aggressive, and don’t let them score.

Keep it legal, of course, but NO. WIMPY. FOULS.

Set the tone. Put your offensive player on their back foot. Make the most of the call.

Small moment, big lesson:

• Start out strong.

• Begin as you mean to go on.

• Make your opportunities count.

• Let people know you’re serious.

It’s okay, in fact, it’s better (!), to be tough, aggressive and assertive. Yep, even as a girl 😉

3. “It’s their job to catch it.”

During one of my high school softball seasons, my dad noticed me throwing softly.

I explained that I didn’t want to hit a teammate in the face.

Some folks had only played a season or two and weren’t super comfortable catching a hard throw yet. Totally normal when you’re learning! I was trying to be a good teammate and make it easier for them.

“You should not change your throw. It’s their job to catch it.”

Small moment, big lesson:

• Working to your potential makes others better

• Do your best. You can’t control how others perform.

• Never dim your light! Don’t lower your abilities or standards to accommodate others.

Don’t be sorry or change because you’re good! It’s their job to level up, not your job to lower down.

4. “I knew you could take care of yourself.”

My dad didn’t do any of the stereotypical protective dad stuff.

• No interrogation when I brought a boy home

• No telling me to change my outfit (that was my mom 😂)

• No offering to “take care of it” if someone was unkind

One time I asked my dad about it.

He gave me one of the best compliments:

“I knew you could take care of yourself.”

Small moment, big lesson:

• I was trustworthy.

• I was tough.

• I don’t need my dad (or husband or anyone) to protect me.

• I have all the tools and capabilities to manage my own self and life.

He taught me to pitch inside, foul like you mean it, and keep throwing hard for a reason.

So I had the skills and confidence to look after myself.

Thanks, Dad. Love you.

What lessons did you learn from your dad? Did y’all play as many sports together as we did? 😂 Any small moments that made a big impact?

Happy Father’s Day!

I was a pregnant startup CEO.

All the startup chaos plus adding a baby? No problem. 😅😳

Fast forward 10 years, I have two adorable boys, a job I love as a tech investor, and a looooottttttt of lessons learned along the way.

Here’s what I wish I knew when I got started…

1. There’s tradeoffs. And that’s okay.

You may not be able to do everything that you did before. Full stop.

I haven’t done an Ironman since having kids. I’d rather spend time with my kids on the weekend than ride 100 miles. I feel absolutely at peace with that decision.

(Because I still get my fix through marathons which take a fraction of the time! 😉)

I do fewer work happy hours and social things. I don’t read as much business news. I see my friends less often.

That’s okay!

I AM RAISING THE NEXT GENERATION OF HUMANS AND THAT HAS VALUE!!!!!!!

Life changes but it’s okay!

You’ll figure out how to keep what’s most important. And let go of the rest.

2. Focus on high leverage activities.

Kids force you to focus. Less chitchat at the watercooler, more getting shit done.

You’ll often hear working parents say they got more efficient, more strategic, and cut the fluff (that they didn’t realize was fluff).

Don’t just “do work.”

Be intentional with your time and energy:

• What are the most important, highest value activities?

• How do I get the most bang for my buck with anything I spend time on?

Examples:

• 1 small group lunch instead of 5 coffee meetings

• 1:1 meetings for ideal customers only, no random LinkedIn connections

• write a blog instead of emailing 1000 people every week 😉

• take photos at events so it’s a social post plus in-person relationship building

• exercise while networking (Founder Funder Jogs!)

• say no sooner and more often

P.S. You should be thinking strategically about your time and energy anyway but kids make it absolutely necessary. 😜

3. Don’t over-explain your time.

I’ve said it before, I’ll say it again:

You don’t need announce to the company that you’ll be offline for 15 minutes while you pick your kid up from daycare.

Just do the thing and then get back to it.

I know it’s good to communicate. And some jobs you truly can’t be away, like surgery or rocket launches.

But for most of us, especially working moms, we overshare the minutia of our schedules with disastrous results:

• You are available and reply to everything asap unless otherwise stated.

• You have no flexibility in your schedule aka an essential component of working parenthood.

• You inadvertently create a work prison of your own making!

When I came back to the office after my first baby, I felt like I couldn’t take time away for pumping:

It’s too much time. I’m gone from my desk. Everyone is wondering where I am.

But like most things — I cared and worried a lot more than anyone else did!

The reality is that no one is available all the time because they’re:

• on an important call

• at a client meeting

• attending an offsite ⛳

• eating lunch

• scrolling social media 😜

So get your stuff done. Do good work. Log on later if you need to reply or finish something. But don’t wear yourself out justifying every minute of your day!

4. Not all jobs are the same.

All previous advice assumes that your company is reasonable and modern.

Examples of normal:

• Open to flexible scheduling if it’s better to arrive early and leave early.

• No problem to take time off for an occasional family vacation.

• Work from home if a child is sick.

• Support for being the Mystery Reader!

Maybe they aren’t family friendly yet (you’re the first woman on maternity leave, for example…) but leadership is open and listening to feedback.

And then…there’s companies that really do suck. They don’t care. They’re not changing. They want you at your desk 80 hours/week, no exceptions.

REMINDER: It’s your life. You don’t have to work somewhere terrible!

Make a change. Find something else.

Or better yet, create the company you want to work at!!

5. Set boundaries. Then follow them.

Usually the person who is least respectful of your boundaries is you.

(Or your children. LOL.)

Boundaries — aka something within your control — can make the difference between loving your job and wanting to quit.

The biggest reason for burnout is having too much to do.

That’s often, at least partially, self-inflicted.

Boundaries are mix of:

• getting comfortable saying no

• having regular non-negotiables

• sticking to a general schedule that works for you (and your family)

My favorite way to handle boundaries is not a big fancy announcement but just casually and consistently make it “your thing.”

(You know how I feel about evening events and getting to bed early! 😉)

These are all real things I’ve heard people say about well-respected, successful founders or executives:

• She’s not available until 9a.

• He doesn’t have his phone with him during workouts.

• He’ll work from the lake house with his family during the summer.

• She logs off at 8p.

• She’s coaching her kids’ sports then.

• He volunteers at his kids’ school every Friday afternoon.

What do those executives say when they’re “enforcing” those boundaries?

They’re using one of these lines!

What do you wish you knew before becoming a working parent? What was the hardest lesson you learned? The most helpful one?

I said it last week.

The key to successful founders (and life!).

But — there’s so many distractions!!!!!!

Especially if:

• The important thing is going to be hard, take a long time, you don’t know how to do it, or all of the above!

• You’re a parent, spouse, pet owner, cool aunt aka have other life responsibilities

• You’re like 99% of founders and have ADHD (a fictional stat but directionally accurate)

• People ask you questions all day aka constant interruptions

• Your creative brain keeps giving you more good ideas

• Your office needs to be reorganized (me, anytime I have a hard project)

So how do you actually force yourself to do the hard thing?

Here’s 10 simple ways to create accountability and get-shit-done energy for the things that matter!

P.S. I’m assuming this important thing can’t be delegated and you’re not the bottleneck. But you should double check on that. 😉

1. Use procrastination to your advantage.

One of the most eye-opening and helpful blog posts of all time from John Perry.

If you’re a procrastinator, don’t fight it.

Trick your self and use procrastination to get stuff done!

tl;dr — when you’re avoiding the top priority, you get all the other stuff done. Then when you have a new top priority, you’ll get the previous top priority done.

2. Identify what you’ve been putting off.

I do a monthly audit with a few questions that I got from Sahil Bloom.

Recurring invite on the calendar. 15 minutes.

One of the questions is:

What am I actively putting off or dreading?

Sounds crazy but usually just naming the thing makes me realize:

a) Oh wow, that thing has been on my to-do list for 3 weeks and it’s not that hard so I should suck it up and do it and stop being a whiny baby.

OR

b) This isn’t really that important and I’m not going to do it so might as well stop pretending and move on with my life.

Either way, it’s a win!

3. Company goals with mid-quarter check-ins.

The ultimate accountability and getting shit done tool.

Setting goals is, of course, a key part of doing important things (even when you’re short on time). Gotta know what the end game is!

Then schedule **a mid-point check-in** ←the MAGIC ✨

Inevitably fires pop up and the day-to-day happens.

People (even founders) lose sight of strategic priorities.

With a pre-scheduled, halfway-point meeting (usually mid-quarter), you have time to course correct and re-focus!

4. Deep work time or 1 day/week no meetings

Even if you’re highly motivated and efficient, when your day is 10 minute chunk of “time confetti,” you won’t move the needle on important things.

I LOVE a company policy (you’re the boss) of 1 day/week of no internal meetings.

(Here’s how to have fewer meetings!)

The team has more time for deep work.

YOU have more time for deep work.

Everyone is happier and more productive!

5. Use an accountability buddy or group.

Entrepreneur’s Organization, Braintrust, group fitness, team sports, school, and 100s of other examples.

Create regular time (with friendly, supportive peer pressure) to foster improvement and accountability.

Rule #1 of racing: people run faster times when they have competition to push them.

Make the hard thing easier by joining or creating your own accountability group!

6. Pick 1 thing.

Here’s how to not get important things done: have 12 important things.

(Try this Priority Matrix to actually determine what’s important.)

I personally love and use a 3-item to-do list.

But sometimes even that is overwhelming.

Enter: ONE THING.

Pick one thing. Make it bite-sized even.

Do the one important thing day after day and all the sudden you moved a mountain without realizing it!

7. Set a defined time to work on it.

I love calendar blocks!

Need to get something important done?

Put it on the dang calendar!

You don’t miss meetings. So treat it like a meeting.

(Now you have to do it but at least you have time!)

Bonus: invite someone else to the calendar invite who will check in or work alongside you.

8. Keep it short — “I only have to spend 10 minutes.”

I use this for workouts, blogs, cleaning the kitchen, writing hard emails.

“I’ll just do 10 minutes.”

Jokes on me though because once I get started, I usually keep going!

Once in a blue moon, I’ll stop after 10 minutes. And it’s great. I’m glad I tried. I fulfilled the goal. I’ll revisit when I have more energy and momentum.

9. Add more constraints.

If you’re trying to get something done —OR— looking for a more creative output, you should give yourself more (even fabricated) constraints.

I am loving David Epstein’s new book Inside the Box: How Constraints Make Us Better about how great creativity often comes from limitations not unlimited possibilities.

• Five Rules for Getting Out of Your Own Way (article)

• Why Too Much Freedom Is The Enemy of Success (podcast)

10. Make yourself the Directly Responsible Individual.

Give yourself some pressure.

Tell your teammates you’ll do it.

Your name, and only your name. (Two owners of a task or project and no one owns it.)

You might let yourself down, but YOU WON’T DISAPPOINT THE TEAM!!!!

This works especially well if you an Obliger (a la Four Tendencies) aka the ultimate team player and helper.

Share your tips! How do you get ‘er done, especially when the stakes are high and the work is hard?? What strategies or tips work for you?

They have big dreams, good ideas, and high motivation.

So what are the best founders doing differently?

Obviously market and idea selection matters (A LOT).

But even in great markets, how a founder executes day-to-day makes a huge difference in company outcome.

Here’s 5 habits that I see consistently across highly successful founders.

1. Work on the important things

So many shiny objects and competing priorities in a startup.

The best founders are able to tune out the noise and focus on what matters.

Doing the things that only a founder can do.

It varies based on company stage but it almost always involves: selling, funding, strategic planning, and hard conversations.

That’s how the business moves forward.

#Protips

(Pick your faves)

• Procrastination (seriously!)

• Decrease meeting creep

• Remove yourself as a bottleneck

• Prioritization spreadsheet

• Post-it notes and calendar blocks

• Effective annual planning

2. Relentless and clear communication

Say it 12 times. Then say it another 12. Then maybe someone will remember.

Such is the life of a founder.

But the best founders don’t mind.

They will communicate clearly and succinctly the vision, values, and story over and over again.

Until everyone in the company knows it. The new hires do too. Customers. Friends. Friends of customers. Friends of friends of customers.

Why?

Because it’s simple and they’ve heard it 1000 times!

#Protips

• Send a weekly update

• Identify and embrace Core Values

• Use a One Page Strategic Plan

• Fine tune a 4 word elevator pitch (start here, you can always make it longer)

3. Emotional regulation

You have to take care of yourself to take care of others.

Every parent has seen this first hand. When I’m tired, I’m more likely to yell at my kids or make knee jerk decisions. 😬😬😬

Ditto for founders.

A founder’s mood is contagious. When you’re positive and steady, the team is too.

If you’re freaking out, reactive, and yelling, that quickly permeates across the company.

I also love this coaching concept from Steve Magness:

“Be opposite the moment.”

If the team is down, you’re lifting them up. If the team is hyped, you’re staying grounded.

Either way, you, the founder, have to be in a good headspace and under control to bring what the team needs!

#Protips

• Take breaks

• Implement healthy micro habits

• Fill your cup

• Founder’s guide to staying healthy

4. Never-ending self improvement

Every great founder is constantly getting better.

Books, executive coaching, peer groups, podcasts — EVERYTHING.

It’s part of their DNA.

It’s also a key strategy for building a successful high growth business.

As Kyle Porter, founder of Salesloft, notably explained:

“You have to learn faster than your company is growing.”

#Protips

• Get exec coaching

• 4 ways to scale with your startup

• Make the move from “founder” to “CEO”

5. Self-awareness

Last but definitely not least.

This quality is what makes all the other habits possible.

Knowing who you are:

• What you like

• What you are good at

• What you are not good at

• What does your company need

• How are other people reacting to you

Read the room! Look in the mirror!

You can’t improve, self-regulate, communicate, work on important stuff…without a pretty clear picture of what works (or doesn’t) for you.

Confidence is important.

Got a chip on your shoulder?

Great. No better way to prove everyone else wrong by building a big, successful company. 😉

But you also have to be open, coachable, and willing to work with your strengths and weaknesses.

How you grow the company, who you hire, core values, likely outcomes — all start with clear self-awareness!

What else? What other common habits have you seen from top founders? What has been the most important habit for you? Any tips on how you implemented or improved one of these??

It’s also hard.

Because — despite my very practical suggestions on 5 ways to build your personal brand and how to get started on LinkedIn, both of which are even easier now after the AIpocalypse — I still get a lot of:

• How do you do it?

• I could never put myself out there!

• I know I should but I just can’t press post.

• It feels so cringey.

Here’s what I wish I knew before I started.

It’s not analytics or posting strategies.

It’s the personal side of personal branding!

1. It’s vulnerable.

The first time you post, it’s terrifying to hit send.

The second time you post, it’s nerve-wracking.

The 100th time you post, you don’t even think about it. 😂

And I’m not even talking about sharing your deepest thoughts.

Voicing professional opinions, learnings, or memories is still putting yourself out there.

So if it feels vulnerable, that’s okay, it’s normal, and it gets easier!

Because the other important thing is…

2. No one cares.

The first time you hit publish on something, you’re like, omg I’m going to have 100 trolls and everyone will make fun of me and I’m going to get fired because something I said with good intention is misinterpreted.

But only your 5 closest friends saw the post! Algorithm FTW.

Even when you’re posting regularly and getting some traction, people are still only skimming and thinking about their own lives.

Maybe they jot off a quick comment.

But they don’t notice “their” instead of “there,” your (always) wild bangs, or that you forgot to tag someone.

If they do, they forget one second later!

3. You control the controversy level.

I was sure the trolls would come for me.

One time they did.

But it wasn’t trolls.

It was…LAWYERS!

(Oh heyyyy nice lawyer friends who read this 👋👋 That was a JOKE! You’ll see where I’m going with this in a minute…)

I wrote this blog about keeping it scrappy on the legal front as a startup. In my LinkedIn post, I wanted to try out a little bit of 🔥🔥🔥 so I opened with:

Look at all that engagement:

But 90% was from lawyers telling me how terrible my advice was! Whomp whomp.

The marketing performance was amazing.

My personal stress levels were not.

It was the first post I ever wrote where people were kinda mean and angrily disagreeing.

I learned important lessons:

• I don’t like being controversial.

• You have control over how controversial you are.

• Never argue with lawyers. 😂

Some people love to shake things up.

It’s powerful and interesting to have a contrarian perspective.

It’s also a great strategy for going viral and getting engagement.

I love that. I respect it. And it’s definitely not me.

But the good news is that I have very few (public? 😂) haters because it’s hard to troll someone who is generally positive.

So take that, haters! (jk jk jk. no controversy here.)

4. Other people can help you.

The 100% absolute best thing ever was working with Confetti Social.

I know and adore the founder, Evie Lutz. She “gets” me.

Confetti Social helps with ideas and copywriting for LinkedIn and Instagram based on blogs, photos, and other stories or insights I share.

Content gets scheduled and auto-posted.

I don’t have to decide which photos to use (a 30 minute task when left to my own devices).

I don’t have to agonize over word choice or other silly things that don’t matter because no one cares (See #2).

Having some separation from the go-live of a post helps a ton with speed, objectivity, and worrying about the performance of any single post.

Whether it’s AI, an intern, an agency, or pre-scheduling everything, creating some systems that give you emotional distance can be helpful for any recovering liberal arts grammar nerds perfectionists out there!

5. The cringe goes away.

Posting content on the internet — ESPECIALLY SELFIES — is cringey.

Agreed.

But now that I’ve:

• done it 500x

• connected with thousands of great people because of it

• realized that I like other people’s photos so they probably like mine

• added value to events, companies, and initiatives by sharing photos and stories about them!

I don’t feel cringey. It’s just the norm. Most people appreciate it. And those who don’t aren’t on social anyway!

6. Don’t be famous.

Luckily, I read this amazing article from Tim Ferris right before I became a global sensation:

11 Reasons To Not Become Famous

It’s easy to chase numbers without realizing what you want.

I am thrilled to have a kind community of folks who care about startups, the Southeast, tech, and wellness!

I want to know and be known by anyone who likes those things.

And since it’s not millions of people (yet), I can safely go to the grocery store without sunglasses and autograph requests.

Whew!

7. You have instant rapport.

I met a great founder who said:

“I know this sounds weird but I feel like I know you because I follow you on Instagram.”

A dream come true!!

No awkward “So what are you working on?” questions.

Just right into the real stuff because there’s a level of trust and comfort.

We can talk about money, compare notes on startup hiring, and trade kale recipes all within the first five minutes!

The downside, of course, is that sometimes I meet people briefly and forget their name or context.

But they can never forget me!!! (Even when they want to.)

I follow them around the internet with my face in their LinkedIn feed and The O’Daily in their Tuesday inbox.

Sorry in advance and please take pity on this tired mom brain and tell me your name again!

8. It works.

People did tell me this before I started.

(You were correct, Shannan Brooks!)

I knew it on an objective level.

But I didn’t really know.

I talk to people almost every day who will mention the blog, LinkedIn posts, or Founder Jog videos.

Or they’ll say, “I see you all the time in my feed” and then I jokingly but seriously apologize. (Also #sorrynotsorry that’s the algorithm y u clicking if you don’t want selfies and momjokes?!)

Here’s the magic:

It’s a conversation starter.
A connection point.
A way to stay in touch.
Be helpful.
Make “investors” less intimidating.
Share trends or lessons I’m learning.
Answer common questions.
Talk about special events or great founders.

And — most importantly — it makes the hard work of startups and life a little more fun! ✨

Thinking about posting more or building a personal brand? YES! I support you!

Would love to hear any other tips, learnings, or questions in the comments or reply to the email.

I’ll happily share any and all personal brand secrets.

(P.S. Biggest secret is…consistency over time. UGH. Laaaaame. 😉)

It’s a great gig if you can get it.

Be the preferred vendor — fractional CXO, talent partner, outsourced accounting, marketing agency, implementation partner, executive coach — for a VC firm.

Ongoing referral business from well-funded, high growth companies? Yes please!

How do you actually make that happen?

I can’t speak from the consultant side, but I can share what I’ve seen work from the venture firm perspective.

Just like cold outreach strategies that work, it IS possible to break into the referral network of an investment firm.

Here are the two strategies I’ve seen work. (And please share below if you have others!! 👇)

1. Help a Portfolio Company

Just like the best warm intro is a founder within the portfolio, the best vendor referral is a happy company.

The simple (but not easy) playbook:

• Provide tons of value to a portfolio company

• Ask the CEO to send an email recommendation on your behalf

This is the gold standard.

If a vendor or consultant comes to me, I say, help a portco and then I can recommend you to everyone!

This is how I knew that Beata Rouleau and Margaret Weniger were awesome.

Rave reviews from founders I know.

Startup Example: Pardot Implementation Partners

As Pardot grew exponentially, we had trusted partners who would do customer implementations.

How did they become trusted?

Because clients used them for other marketing consulting projects and told us they were great!

The best path to a great long-term partnership of any kind? Help customers!

2. Someone Who Knows Your Work Product

Until last month, I thought there was only one way in.

I LOVE BEING WRONG!

I shared my “intro from a portco” strategy and a founder told me that he was getting recommended by a PE firm without helping a portco first.

Whaaaaa? 🤯🤯🤯

“How did you get connected to the firm?”

“I worked with one of the partners at my previous company.”

BOOM. Duuuuuuh. Of course!

If you have worked with someone previously, they already know your personality, work quality, and impact.

Fantastic entry point!

It’s what I recommend to anyone first venturing out as a consultant:

1. Reach out to people you’ve worked with before.

2. No need for a perfect sales pitch. They know you.

3. Get some gigs through your contacts.

4. Now you have experience, happy customers, and a refined value prop!

Startup Example: Fundraising Strategy

This strategy applies to raising early capital too!

You might think that the wealthiest person you know (however distant) is the best option for a check, but you’re much more likely to raise from people who know you best.

I know founders who raised from college professors and church pastors.

The power of personal connection and lines over dots!

But, Kathryn, You Know I’m Awesome! Why Can’t You Recommend Me?

There are a lot of vendors and consultants that I really like and I’m sure they’d do a great job.

I know them through events, warm intros, or other trusted communities.

But I haven’t seen their work up close.

What if I referred a founder and the consultant did a bad job???

LITERALLY MY WORST NIGHTMARE 😱😱😱

Wasted money and time — because of me????— when startups are already tight on both.

Even if I know someone is great, it may not work out.

But at least I have a clear conscience on the leading indicators of the recommendation (aka I’ve seen their high quality work).

The other calculation I’m doing is time-to-verify.

I could do a deep dive reference check on every vendor —> hours of work.

Or I could read one glowing review email from a founder I trust —> minutes!

Are There Any Exceptions?

Always. 😉

1. The “Jane McCracken” Effect

When I was thinking of exceptions, I literally thought of Jane!

I haven’t worked directly with her but she’s built 3 companies and taken at least 2 of them public so, yea, she knows what she’s doing.

Sometimes people’s resume and personality are so good that you’ll recommend them no matter what!

2. Work On Display

Social media and brand building is an area where someone’s work is public.

Can they do it for your brand? Maybe, maybe not.

But you can see their work in real time so it’s easier to evaluate!

Ditto for outsourced sales, talent agencies, website design, etc.

3. Area of Expertise

The more direct experience I have with a job function, the easier it is for me to evaluate someone.

I’m much better at sniffing out Customer Success or COO competence than other roles.

4. Help a VC

If your service is relevant for the VC firm, you could help the firm as a way to showcase your value.

When Rebby John of Fastlane AI spent an hour talking to us about AI best practices, my mind was blown from the awesomeness.

(Fastlane AI is an Atlanta Ventures Studio Company so it was a different circumstance but I could see how it would work!)

Beware of spending too much time on anything where there’s not a fully paid engagement or deep pain point though…

You might end up with a disengaged or unimpressed VC firm which undermines the whole strategy!

Have you worked with any amazing consultants or vendors? What won you over? What’s your advice for vendors or consultants who want to “break into” startups or investing firms?

True for anyone you want to meet and definitely true in the wild world of venture capital.

The gold standard intro is from another founder in the portfolio. (Here’s why.)

After that, any warm intro is great.

(“Warm” intro means mutual acquaintance of some form introduces you.)

If you can’t get a warm intro, do cold outreach.

BUT - for goodness’s sakes - make it thoughtful and personalized!

A.T. Gimbel and I preach this on Office Hours and blog posts.

I can give all sorts of examples of cold outreach that doesn’t work. (I delete dozens of unpersonalized, form emails every day.)

But that’s not as helpful as seeing what DOES WORK!

Here are 4 examples of real cold outreach, why it worked, and what happened next…

1. Cold Outreach via LinkedIn

Ellen Twomey is one of my favorite startup folks and it came from a simple LinkedIn message…

How it started:

What worked well:

• She said “moving to Atlanta”

• She said “founder”

• She said “closing the gender gap in tech”

• Short

• Included email so I could look her up and/or take the convo off LinkedIn

• She made an ask but it was low key

What happened next:

• I replied.

• We had coffee.

• Coffee was really fun.

• We’ve stayed in touch! Emails, texts, events — we connect every few months and it’s always delightful.

2. Cold Outreach via Website Form

“‘Contact Us’ forms on websites never work…” - says everyone but Paddy McNamara.

How it started:

What worked well:

• Moving to Atlanta + explained why

• Specifically mentioned Atlanta Ventures without being totally generic

What happened next:

• When we replied, HE FOLLOWED UP!

• We chatted.

• Then HE FOLLOWED UP AGAIN!

• Now, he regularly replies to blogs, shares company updates, reaches out for advice, and proactively stays in touch!

The Magic:

Paddy shared that both of his parents are teachers and he didn’t have connections to tech or business when he started.

What he did works for anyone regardless of their network:

1. Personalized cold outreach

2. Follow up in a responsible, appropriate way (not asking for money or aggressively pitching)

3. Immediately start building a relationship

4. Stay in touch over the years

3. Cold Outreach via Email

The inbox is a black hole. Mostly true. But occasionally an email rises to the top, like this one!

How it started:

What worked well:

• Personalization — clearly has taken time to research and write a thoughtful email

• Said the magic words: “Run.” My days are filled with founder meetings. I frequently get asked to grab coffee for career networking. I like these conversations but, unless it’s someone who might be a fit for a current portfolio company, I pass so I have time for founders!

• BUT — I like running with friends. So if someone thoughtful and responsible (evidenced by the personalized email) will drive to Decatur at 5:30a for a 6 mile run at 8:30 pace, I am available!

The Magic:

• EVERYONE HAS A MAGIC WORD.

• The thing you can say that will induce them to open an email, reply, take the next step, make time in a busy schedule.

• Examples: Manicure, golf, wine tasting, hair blow out, walk, sauna, heli-skiing, coffee shop near their house, providing dinner for the family, same college or high school, favorite athlete, obscure hobby that you have in common

• It will vary depending on the person, but if you figure it out, it’s a huge unlock!

4. Cold Outreach via Event

How it started:

I did a presentation at Atlanta Tech Village. It’s pretty normal for a bunch of folks to say hi afterward.

One woman shared that:

• (a) we have the same name (yes, it’s Kathryn Farrell! Kathryns unite!)

• (b) my story about Ironmans resonated since she was a D1 runner.

I asked where she ran. University of Florida.

Just so happened that she knew my husband from her college track and field team!?!

What happened next:

• It could have ended there but she followed up.

• We went running. (See #3 for my magic word.)

• She was a reliable and interesting running partner.

• She was working in healthcare but wanted to work in tech.

• I wanted to get better at running.

• Fast forward 3 years, I’m a faster runner and she’s a tech CEO 😉

What worked well:

• Saying hi after an event. A great time to make an impression, especially if you are “breaking into” a new industry.

• Leveraging charisma. The whole premise of Personality Pool! Especially when resumes (or LinkedIn profiles) don’t capture the full story.

• Capitalizing on connection points — same name, sports.

• Knowing my husband was an unexpected bonus uncovered via conversation.

• FOLLOW UP!!!!!!!

The Playbook

Are you seeing the commonalities?

• Personalized outreach.

• Follow up.

• Focus on human connection.

• A little bit of timing and magic in your favor. 😉

Trying to get in touch with someone? Use these tips and keep going!

What is your best cold outreach strategy? What’s worked on you? Anyone that you cold outreached that’s now a friend, customer, or business partner?!? Share the story!

And no, it wasn’t Claude. 😂

It was Rebby John, the incredible founder and CEO of Fastlane AI (spoiler alert: Atlanta Ventures Studio company!), who helps mid-size companies understand where and how to get started with AI.

What can startups learn from mid-size companies using AI?

A lot actually!

Here are the top tips from Rebby on what to do (and not do!) to make the most of AI at your company!

4 Dos For Implementing AI

1. Do identify where you are.

Two types of companies:

1. Know what they want. Need manpower or expertise to execute.

2. Know they “need AI.” Don’t know what’s possible or where they should start.

3. Not sure they want or need AI. Literally does not exist anymore. Use or perish! (Note: startups have known this for a while 😉)

Which category do you fall into?

It’s good to get clarity (and be honest with yourself).

Different plan of action for each!

2. Do put your best people on it.

How do you succeed with AI?

Put your best people on it.

Even when they have other things that are really, really important, the successful companies are taking their best people and reallocating them to AI projects.

At a large company, your best people are your busiest.

At a small company, everyone is the best and everyone is busy. 😂

BUT…the idea is that companies using AI successfully are making intentional tradeoffs.

Have no time?

Make time. THIS is the important project.

In Startupland, it means deprioritizing very important things for AI.

Painful in the short term but worth it 10x over long term!

3. Do expect multiple iterations.

“AI is not good and really annoying” - me, in 2022, after one try with a terrible prompt.

Reminder to all companies — don’t be like me! 😁

Of course it wasn’t good. I expected perfection on the first go round.

The best companies understand that the first implementation is not the final outcome!

One great thing about AI is how quickly you can refine and tweak.

Companies willing and planning to iterate will have the most success!

Startups already know this deeply. 😂

The more you expect to suck the first time the faster you can get better!

4. Do rethink the process.

2X BETTER: Take current process. Add AI.

100X BETTER: Change the whole workflow!

Companies see most value when they’re willing to reimagine what’s possible.

• If you were starting from scratch, what would it look like?

• If you had no employees, what would you do?

• If you could only use AI, what would be different?

Broaden your perspective to get the most out of AI!

4 Don’ts For Implementing AI

1. Don’t expect AI to do everything.

Love this action step from Rebby:

Make a list of pain points, manual tasks, any areas AI might be able to help with.

Then get honest about what AI can and can’t do.

Put your list in an AI tool or ask an AI expert for feedback!

AI is great, wonderful, amazing, but it can’t do everything and some things are going to be faster, easier wins than others.

Better to know that up front so you don’t force it! (Or drive yourself crazy 🤪)

2. Don’t make it harder.

Yes, custom agents are cool. But if there’s a SaaS tool that can already do it, no need for agents.

Opt for simplicity!

I love this decision flow from Rebby and Fastlane AI:

tl;dr: use SaaS → SaaS can’t do it? Use no-code/low-code automation → Low-code can’t do it? Build custom agents.

3. Don’t judge based on technical ability.

One of my favorite stories about AI implementation from Rebby was a woman who was not technical, held the same job for 30 years, and she figured out how to automate 75% of her daily tasks using AI!!!!!!!! 🤯

Did she work herself out of a job?

Kind of.

She got promoted!

Fastlane showed her how to use Claude to write Python scripts and she was off to the races.

What used to take 2 hours took 2 minutes.

That’s the ah-ha that makes people believers.

It’s not only engineers or tech-saavy folks.

The most important qualities for AI success?

Willingness to try and openness to learn and iterate!

4. Don’t decentralize AI agent creation.

Give everyone the keys to the AI castle! Build whatever agents you need!

In theory, yes.

In real life, it leads to lots of half-baked agents that aren’t helpful.

Yes, you want everyone to have access to approved and connected Gen AI tools (e.g. Claude or Gemini team account synced with your Google Workspace).

Yes, you want to decentralize identifying agentic AI use cases.

But companies get more value when the responsibility for building AI agents is centralized.

At a mid-size company, it’s a Center of AI Excellence, a hand-picked team that builds, verifies, and rolls out AI agents (and other AI initiatives) to the company.

At a startup of 10+ people, designate a “directly responsible individual” to create agents so your team’s AI implementation is working and aligned.

Yes, everyone is using AI and you want people to be empowered and sharing ideas.

But from the front lines of AI implementations, Rebby sees a truth we all know well:

Ownership and accountability result in higher quality output!

What has worked for your company?? What’s your best AI tip? Do you have a favorite Gen AI tool or use them all?!?

The topic?

What founders need to know about raising capital in 2026 — what’s the same, what’s different, and the tactical tips that top founders use.

Here is the FULL SLIDE DECK with a bulleted summary below and some photos!

Not included in the summary:

• Say your First Name, Last Name, Title, and sound awesome (our warmup!)

• Great audience questions!

Check out what the brilliant and talented Heather Gibbons shared, like, 12 minutes after the event ended:

SUPER AWESOME SUMMARY (that’s definitely better than this one!)

If you’re feeling a little FOMO…

• Upcoming Spring 2026 events

• Forever link for Atlanta Ventures events

See you at next fun thing!

What Founders Need To Know About Raising Capital in 2026

Same As Always

True in 2006, 2016, 2026

What Venture Investors (Still) Look For

• Big markets ($100M in revenue)

• Authentic demand

• Ambitious founders

What Successful Founders Have In Common

• Learning

• Selling

• Resilience

• Authenticity → be the best version of yourself! Foundership can look different.

• BIG MARKETS!

A Whole New World

What’s different (and working) in 2026

But Wait…Software Moats

AI is disrupting traditional software — but moats still exist!

Straight from David Cummings recent blog which came from Gokul Rajaram on 20VC.

Moats to look for:

• Data

• Workflow

• Regulatory

• Distribution

• Ecosystem

• Network

• Physical Infrastructure

• Scale

Want to see it in real life? Check out Infinite Giving, Greenzie, Carpool Logistics, and AdPipe!

So Hot Right Now

• In-person + physical world businesses with AI efficiencies (Dandy, January)

• Robotics (Undaunted)

• AI consulting (Fastlane AI)

• 99% AI businesses (Reframe, Interlock Studios)

How To Raise

Tips and tricks that top founders use

10 Fundraising Pro Tips

1. Lead with money!!!!!!!!

2. Confidence. Fake it ‘til you make it.

3. Go to Pitch Practice → pitchpractice.co

4. WATCH: The real reason female entrepreneurs get less funding (Dana Kanze — TED Talk)

5. Prep for Q&A

6. Pitch your worst first

7. Lines not dots

8. Investor fit — who has $$ that cares about this problem?

9. Metrics: yours + industry benchmarks. BONUS: look at public companies in their early days

10. Read the O’Daily 😉 (hehehe. You already completed this one!)

#1 Capital Source

True in 2026 & always

Customers that pay you!!!!!

Get Paid Without A Product

• Design partners

• Consulting

• Run (paid) experiments

• Founder creativity

Photos!!!!

#sorrynotsorry for all the selfies. I’m basically a professional photographer but I work for free. Stay scrappy, friends.

What questions do you have about raising capital in 2026? What’s working (or not working) for you right now?

Want More?

• Go Big: The What, Why, and How of Building a Billion Dollar Business

• 3 Fundraising Secrets From a VC

• Show Me the Money: 1 Tip for Pitching

• How to Talk About Revenue When You Don’t Have Much

• 5 Wild Ways To Pre-Sell Your Product

I can’t believe it’s been 5 years since I joined Atlanta Ventures and went from startup COO to early stage investor!

I love reflecting on learnings (and passing them on, of course!!).

Here’s 5 things I’ve learned after half a decade with the awesome crew at Atlanta Ventures.

1. Things Can Change Quickly

Settle in, it’s a long game, they said about investing.

That’s 100% true.

And yet this “long game” involved:

• The Great Exuberance of 2020 + 2021

• The Great Reset of 2022

• AI changing literally everything

• And, oh yeah, internally at Atlanta Ventures, we purchased 10 city blocks in Downtown Atlanta (total transaction time: <6 weeks) and a massive restoration and revitalization is underway for a vibrant, walkable, entrepreneur-centric city center. 🤯💪🙌

You never know what’s around the corner. True for startups, life, and boring ole venture investors! 😜

I wouldn’t want it any other way.

2. Hire Good People & Let Them Operate

Not a new lesson, per se, but no one does this better than Atlanta Ventures founder, David Cummings.

• Available when you need guidance and sets high level direction.

• Builds a team of complementary personalities, backgrounds, and skill sets.

• Gives tons of autonomy and freedom. Says yes to almost everything.

I LOVE working in environments like this.

Some people like more structure, tasks, or direction.

But I, and most startup-oriented folks, follow my kindergartner’s mantra: “You don’t need to boss me!”

Wondering if you’re too in-the-weeds or micromanaging? Maybe you’ve heard about this thing called “letting go” but you’re nervous to try it? (You’re not alone.)

Clarify the goals, explain what decisions you do and don’t need to be involved in, then run an experiment to see what happens when you’re less involved.

With the right expectations, direction, and people, your team will love it!

3. Nice People Rule The My World

OMG IS IT DELIGHTFUL TO WORK WITH NICE PEOPLE.

Here’s what I mean by “nice”:

• Kind, funny, positive

• Trustworthy

• Responsible

• Will communicate a hard thing (to you or someone else) in a clear, thoughtful, respectful way

• Differing opinions are good! Ask questions, express ideas, and offer other perspectives without raising voices or making it personal.

Life is too short for jerks.

P.S. Being nice is also good for successful exits. 😉

4. “You be you.”

Should I get better at spreadsheets? Do I need to do complex math in my head? What about golf? Should I learn to golf?

The answer?

“You be you.”

An awesome thing to hear. (Especially from your boss.)

Another way I’ve heard it said:

“Be the best version of yourself.”

Everyone has their own style and strengths.

Yes, always be growing and learning.

But don’t try to be someone you’re not.

It’s hard, weird, and doesn’t work.

Reminder: this is true for founders also!

I’ve seen unicorn founders who are fiery and outspoken. I’ve seen others who are calm and analytical.

There are many forms of excellence.

You be you.

5. A Lot Can Happen in 5 Years

It doesn’t feel like much progress is happening when you’re in it.

Then you look back and realize how far you’ve come!

5 years ago:

• The O’Daily didn’t exist and now it has over 225 posts and 1100 subscribers!

• My kids were 1 and 3 years old. Now I have 2 kids in elementary school!

• We had 2 Studio companies and now we have 7 (including these)!

• We’ve deployed over $100M in support of entrepreneurship (much, much more if you include South Downtown).

• I was walk-running to get back into shape after pregnancy. Last fall, I hit a lifetime goal of running a Boston-qualifing marathon.

FOUNDERS — what were you doing 5 years ago?!?

I bet you’ve made more progress than you think!

I know folks who hadn’t even started companies yet and now they’re doing millions in revenue!

What does the next 5 years hold?

I have literally no idea.

Check back in April 2031 for an update! 😉

What was your biggest accomplishment over the last 5 years? What lessons have you learned? Any upcoming career or life milestones for you??

But we’ll still clog up your inbox, I mean, offer valuable startup advice!

I’m resharing a post from 2022 on a common founder topic:

Who, what, why, when, how to hire a COO at a startup!

(It’s not what you think…)

NOTE: With the improvements in AI, I would actually update #3 to improving your AI usage vs getting outsourced human help. Things have changed a lot since 2022!

More on AI in the next few weeks! 😉

The COO Search

I frequently talk to founders who are looking for a Chief Operations Officer (COO). These are early stage companies – 5 to 20 employees, $0 to $1,000,000 in revenue, 5 to 50 customers, bootstrapped or small seed funding.

The founder is looking for:

• Another leader

• Trusted resource who can handle mission critical initiatives

• Skills or experience the founder isn’t as strong in (e.g. sales, product/tech)

• Someone who can “free up” the mind or calendar of the founder

It’s hard, near impossible, to find an excellent, experienced, affordable startup COO for a company at this stage.

Do not despair! You don’t need to find your magical once-in-a-lifetime unicorn on day one.

Here are 3 strategies to fill a COO role at an early stage startup.

3 Startup Hires To Make When You’re Looking for a COO

1. Hire an operations manager…that could grow into a COO.

Why buy a sledgehammer when a heavy duty fly swatter does the job? Yes, the very junior folks haven’t worked out. But the range between entry-level ops and COO is vast.

Is there someone smart, hungry, and operationally-minded in your network that could start as an ops manager and grow from there? COOs are hard to find but everyone knows an up-and-coming ass kicker, I mean, operator.

Think: project manager, exec assistant, event planner. Look for a few years of experience in a logistics-heavy role with people or vendor management experience. They will be well-respected, highly recommended, and have moved up quickly. You’ll hear people say, “I trust them to get shit done.”

2. Hire a function-specific leader…that could grow into a COO.

What area of your business could use a leader or more experience? Don’t hire a general COO. Hire a VP of Sales, Head of Marketing, Finance Manager, or Business Development Lead. Pick someone who thinks about systems, processes, and playbooks.

You’ll acquire deep expertise in an area where you need it today AND the potential to develop a COO from within your organization.

3. Outsource to a contractor or virtual assistant.

If someone was managing your calendar, paying invoices, following up on client to-dos, designing marketing materials, running your social media, buying groceries, setting meeting agendas, onboarding new hires –OR WHATEVER ELSE YOU NEED– how much time would that give you?

Not sure what could be delegated? Levels CEO Sam Corcos has 56 tasks that are handled by a virtual assistant. Read this amazing Sam Corcos Starter Pack for inspiration.

But Weren’t You a Startup COO?!?

Is this blasphemy coming from a former startup COO?

Spoiler alert. I was Option #2. I started as the head of Client Success and moved into the COO role after a year. I was motivated, well-prepared, and had deep knowledge of the team and business. The company knew my strengths (and weaknesses - ha!) and moved me into the role with confidence. It was a win-win.

Any other oldie-but-goodie posts I should feature? What are some fave topics? Hope you had a great Spring Break/Easter/Passover/Allergy Season!

Spring in Atlanta has sprung so get out and enjoy some startup events including:

• In-person, virtual, and exercise-related 🏃‍♀️

• Education, founder stories, and fun

• Conferences galore

• Regular monthly events

Add to the comments any events you’re hosting or attending!

Top 3 Must Attend

3 events I’m attending or presenting at! Come on out. Reply if you’ll be there so I can say hi 👋

1. 5 Things Women Need to Know About Raising Capital in 2026

📅 Wed, Apr 15, 12–1:30p
📍 Atlanta Tech Village — Buckhead

I love presenting at Women + Tech and YOU KNOW I’ll be bringing the practical fundraising and startup advice.

Meet other great tech women, eat some lunch, ask lots of questions.

I will overshare with behind-the-scenes stories and things I can’t put in writing 😉

Guys are welcome too!

2. Atlanta Healthcare Entrepreneur Meetup: Founder Stories

📅 Wed, Apr 15, 9-10a
📍Virtual

Join other healthcare founders, investors, and leaders for small group networking and then hear from these fantastic founders:

• Andrew Nye of Qatalyst Health

• Hannah Olson of Disclo

• Amari Morton of Greater Change Health

A.T. Gimbel and Jacey Cadet are always fantastic hosts. Can’t wait to learn what these founders are building and see you there!

3. Founder + Funder Jog

📅 Fri, May 15, 6:45a
📍Tech Square - Biltmore Ballrooms

Join us for a leisurely 3.5-4 mile jog around Peidmont Park with other founders, investors, and startup folks.

Thank you as always to Katie Begando, Denis Cranstoun, and Julie Pierre for hosting. 🙏

Very friendly, lots of selfie stops and shortcuts, with coffee, water, and sometimes snacks (!) at the end.

High Value, Every Month

These are ongoing events that happen monthly or weekly!

Pitch Practice

📅 Weekly
📍Atlanta Tech Village - Sylvan + Buckhead
🔗 pitchpractice.co

Led by the brilliant Jacey Cadet, get *FREE* help on your startup pitch!

Office Hours with Atlanta Ventures

📅 Monthly, usually the 2nd Thursday
📍Virtual
🔗 atlantaventures.com/events

Join me and fellow Atlanta Ventures partner, A.T. Gimbel, for an informal Q&A sesh on fundraising, product development, early customers, and more!

Startup Chowdown

📅 Weekly
📍Atlanta Tech Village - Sylvan + Buckhead
🔗 atlantatechvillage.com/events/upcoming

Casual, catered lunch with other founders and startup folks. Fridays in Buckhead, first Tuesday of the month in Sylvan. Open to all!

If you’re a member at Atlanta Tech Village, don’t forget about Advisor Office Hours. Chat with startup experts in legal, financial, marketing sales, hiring/HR, engineering, and more.

Conference Extravaganza

In-person is BACK and this conference lineup proves it. Just a sampling of what I know about!

Headed to one or many? Follow my world-class advice and make the most of a shoestring budget.

Atlanta AI Week

📅 Mon, Apr 20 - Wed, Apr 22
📍Atlanta Tech Village

Get your AI fix. I haven’t been before but if you want MOAR AI, the lineup, topics, and attendees look 💯!

Seed The South

📅 Mon, May 18 - Tue, May 19
📍Charlotte, NC

Fantastic 2-day capital summit in Bank of America Stadium with funding, education, connections, and fun, brought to you by gWen and Innovate Charlotte.

Sloss.Tech

📅 Wed, Jun 24 - Fri, Jun 26
📍Birmingham, AL

Over 1000 attendees and $100,000 in prize money, Sloss.Tech is a fan favorite in one of the hottest tech scenes in the South.

ATL Tech Week

📅 Sun, Aug 9 - Fri, Aug 14
📍Atlanta

It’s a week-long tech party, each day at a different tech hub across Atlanta. Tons of engineering talent comes to town too. Last year, I spoke about building a billion dollar company during the Atlanta Tech Village day.

3686

📅 September 2026 (specific dates TBD)
📍Nashville, TN

Nashville knows how to innovate and roll out the red carpet. A celebration of entrepreneurship with 900+ startups, investors, and ecosystem leaders, it’s a Southern classic.

Venture Atlanta

📅 Wed, Oct 14 - Thu, Oct 15
📍Woodruff Arts Center

Yes, there will be thousands of founders and investors.

Yes, there will be a jog on Wednesday morning. (Check back or follow on LinkedIn for the deets.)

A sampling of fun from a previous year!

Even More…and Stay In The Loop!

I can never capture everything! What are you looking forward to? What did I miss??

Here are some of my favorite event calendars:

• Hypepotamus Calendar

• Atlanta Tech Village Calendar

• Startup Atlanta Calendar

Find the most up-to-date event announcements (PLUS PHOTO RECAPS!!) on the socials:

• Kathryn LinkedIn

• Kathryn Instagram

• Atlanta Ventures LinkedIn

• Atlanta Ventures Instagram

Comment below with events you are hosting or other events you’re attending that we should know about! 👇👇👇

Best case scenario, fundraising takes 100 conversations and 3-6 months.

I know great founders who had 300 conversations over 12 months before successfully raising. Some do even more never to raise at all.

You’ll hear different philosophies:

• It’s a numbers game.

• Cast a wide net.

• Do a targeted lightning strike.

• Go deep with a few.

• Build a long term relationship.

• Take any meeting. You never know where it could lead.

• Don’t waste your time if it’s not a fit.

So, should you talk to investors who are not a fit?

How do you balance your precious time with the reality of a sales funnel and the magical startup ingredient — serendipity?

Answer: it depends.

Better answer: let’s walk through scenarios for yes, no, and the nuances so you can decide for yourself!

YES! Talk to investors who are not a fit when…

1. You’re starting your fundraise journey.

Always pitch your worst first!

Get some practice. Ask for feedback. Work through the Q&A.

Do this with friendlies who are not a fit for investment.

I’d also do this with non-friendlies (unfriendlies??) before heading to the investors you think are a perfect fit.

You want to bring your A game when you get to those meetings.

You’re not going to play your best basketball on the first day of the season. Save that for March! 😉 🏀

2. You have a personal connection.

Work that network, baby!

I will take a meeting and be helpful to a founder who is not a fit for our portfolio if I know them well or they came highly recommended from someone I like and trust.

The goal for the founder?

To get feedback and see if I know someone who might be interested.

Will we change our investment thesis because of a personal connection? Nope. But I might be able to intro you to someone who is closer to the right fit!

Also, while rare, if an investor has a long term relationship with a founder (known them for years, involved in previous companies), that’s when they are most likely to “make an exception.”

You’re in a weird space.

You don’t fit cleanly into the typical investment boxes of B2B Software or B2B Software. (#momjoke)

No but seriously, maybe you’re medical device-ish selling directly to consumers. Consumer product investors are going to say you’re too medical. Medical device investors will say you’re too consumer.

You will likely have to talk to more investors than someone who is cleanly in one space.

You’re not necessarily pitching everyone for investment.

It’s more of a “I’d love your feedback and if you have suggestions on who to speak with” strategy to grow your network and reach the investor who LOVES the medical device-ish consumer space!

You like them.

I don’t know how else to explain this but if you feel really drawn to someone, even if you’ve never met them, I’d probably take that meeting.

Maybe your lives have a lot of overlap.

You’re both Amherst College grads who love triathlons and have elementary-aged kids?!?

You’re going to hit it off (with me) right away!

I don’t know if this has ever turned into an investment but making a genuine connection with someone is usually energizing and leads to good things.

It’s easy.

“Talk to investors” usually means reach out via email, LinkedIn, a warm intro, and set up a meeting.

That’s very time intensive, especially if that investor is not a fit and highly unlikely to invest.

The math is different if you can go to an in-person event with a lot of investors. Or you meet an investor at an activity that is fun or you were going to do anyway.

(Shameless plug for Founder Funder Jogs!)

Now, don’t go to an all-day robotics event if you are building software for lawyers, but if there’s something that feels like a light lift, you’d have fun, lots of opportunity to run into people and get some face time, that might be worth it.

NO! Don’t talk to investors who are not a fit if…

You think you can change their mind.

The investor has told you it’s not a fit. You take the meeting anyway because you’re awesome at sales and you can sway anyone.

It’s not going to change their mind.

Maybe, MAYBE, this happens .000001% of the time. I’m sure someone has a story but I haven’t seen it and I wouldn’t take those odds.

If an investor has already told you it’s not a fit, they are trying to save you time and heartache.

One less emotional rollercoaster to ride.

Believe them. Use that time on higher ROI activities.

It’s cold outreach.

You cast a wide net and sent a canned form letter to an investor who is very far outside your strike zone.

They invest in clean tech software. You’re a consumer dating app.

A brand new entry-level analyst might take the meeting. (A more senior one would not.) Maybe they have metrics they’re trying to hit.

But it’s not going anywhere because it’s not a fit for them and there’s no personal connection or business overlap!

A waste of 30 minutes plus your prep and follow up.

Better to spend time finding a warm or more targeted option.

The fundraise is not going well.

Things going reaaaaal slow? Like, you talked to 500 people over 12 months with no bites?

It’s tempting to take any meeting you can get. Are you a friend of a friend of a friend of someone who invests? Let’s talk!

Obviously, there’s a balance. You’re going to hear a lot of “nos” and if you’re in a “weird space” (^^in the YES section), it may take more conversations.

But if you’re having trouble fundraising, talking to even more, random investors is probably not the answer.

These are the circumstances when founders get taken advantage of, end up with someone shady or mean, or have a toxic investor relationship that hurts the company’s long term trajectory.

The best use of time?

• Pull back and regroup!

• Get more customers and traction.

• Pivot your market or idea.

• Figure out other funding sources like consulting revenue or customer prepays.

Spending a few months focused on the business will be great for your company and usually makes the next fundraising cycle easier.

How do you decide to take an investor meeting? Do you agree with the Yes and No scenarios? Have you seen another strategy work well? Share your tips and advice! 👇

Want more content on fundraising? What questions should I cover? Reply and lmk!

InVenture Prize (self-proclaimed “American Idol for Nerds”) is a entrepreneurial competition at Georgia Tech on live TV with $35,000 up for grabs.

Over 72 teams enter the competition with the best 6 in the final televised competition.

THESE STUDENTS ARE AMAZING!!!!!!

(Recap here, full show here, team overviews here!)

Here’s what I was doing in college: planning and attending parties.

Here’s what they’re doing in college: building businesses and competing on live TV to fund their company.

What makes these “kids” special? What are they doing that we can learn from?

Here’s what I saw last Wednesday night.

1. They really want to be founders.

The longer I’m in this world of entrepreneurship, the more I’ve come to believe that the most important quality of an entrepreneur is…

They really, really want to be an entrepreneur.

You don’t need to be the smartest, the best at sales or (vibe)coding, or have the deepest network.

You DO have to want it so bad that you are willing to do what others are not.

Like I mentioned before, these students are doing different things than many college students (myself included 😜).

They:

• spend hours outside of school and extracurriculars on their company

• pitch on live TV (with practice, practice, and more practice to get it right!)

• talk to everyone and anyone - customers, experts, enterprise companies

• pass up fancy internships and big name jobs

• care more about their company than their GPA

• wear capes, talk about vaginas, ask for business

Simply put — they want it enough to do whatever it takes.

They bring the energy and it’s contagious!

2. They show up for help and take advice.

These students brought their A game.

The pitches were as good or better than any I’ve seen.

Did that happen automagically?

No way!

Hours of prep and coaching goes into the 6 minutes we see on stage.

These founders:

1. showed up for practice sessions

2. got critiqued by many people

3. took the advice

4. practiced

5. repeated 1-4 over and over

SO many people and organizations are available to support founders.

(Shout out to the many professors, administrators, and mentors at Georgia Tech who gave hours of their time to help entrepreneurial students! 🐝 )

These students did what many do not — utilized (and listened to) the experts available to them!

3. They are getting the reps in.

Think you want to start a company some day?

Do it now!

Don’t get related experience.

Get the actual experience.

Because there’s so much that you can only learn by being the actual, real, full-on founder of a company.

(You’re going to suck at first, might as well get that part over with!)

Regardless of the business outcome, everyone on the stage (reminder: in their teens or early twenties!) has already learned invaluable entrepreneurship lessons that you can only get from doing.

Maybe they learned they didn’t like it 😂

Many of the companies on stage have already iterated their business multiple times based on market feedback.

“Market feedback” is code for: no one liked or bought it, someone else already built it, they got a cease and desist, you know, the startup usual!

Whenever I talk to an amazing young founder, I find out they have been building businesses for years. Did neighborhood errands, jewelry making, lawncare, online selling, or all of the above.

(True for engineers too — many great college-age engineers have been building for 10 years already.)

It takes time and experience to be great.

Every rep — regardless of the outcome — provides invaluable learning.

These students are getting the reps in!

4. They’re on the forefront of innovation.

You know who’s using AI?

College kids.

Just like they have always done the cool and innovative things first.

(Facebook — aka social media — started in colleges, I was there 👵)

They are time-rich, asset-poor, and immersed in a high-density social environment which leads to tons of creativity!

AI specifically is amaaaaaazing if you are tight on resources.

One startup was delivering their software for $30/mo!?! It was very niche (software for muralists) but if costs are low, you can go after a niche market that wouldn’t have made sense before!

These students are AI-native and will be building successful businesses faster with fewer humans than ever before.

Today it’s AI. Last decade it was mobile. Before that, Internet.

What’s next? Who knows?

I do know that great founders will be innovating around it.

Because every great founder — young or old — is curious, thinking outside the box, testing the new thing, and looking towards the future!

What trends or lessons have you learned from student entrepreneurs? Did you catch InVenture Prize? What are your fave pitch competitions??

MORE PHOTOS 👇👇

It’s time for the big move…

From player to coach.

(Or maybe even from coach to general manager!)

When the company starts to grow, you go from founder to CEO.

You, of course, still are the founder too (lest we trigger another “Founder Mode” debate).

But when long term planning goes from “tomorrow” to “next month” (#startupjoke) or the team grows from 1 to 10 to 100, your leadership role evolves.

This change requires:

1. Emotional work

2. Tactical strategies

Let’s walk through it so you’re ready to embrace your CEO era with grace and world domination.

From Founder to CEO: Inner Work

Start here. The emotional work can be harder than any product challenge or sales deal.

1. Trust your team.

This means:

• Handing off projects

• Being okay with mistakes and a learning curve

• Knowing they won’t do it as well as you can…in the short term. But long term it will be better!

• Hiring great people

2. Get your head right.

Feeling insecure because you’ve never done it before?

Join the club.

Every successful person feels Imposter Syndrome.

• Acknowledge the feelings.

• Notice how they manifest (tackling easy tasks instead of important work???).

• Then get yourself fired up for the next level.

You figured it out before. You’ll figure it out again.

(P.S. Here’s 4 strategies that top CEOs use.)

Remember — when you started out, you were dying to have this “problem” of how to scale! 😉

3. Understand the new job.

You got promoted.

You went from individual contributor to coach. Maybe even general manager.

Coaches can’t throw the winning pitch. General managers don’t even step onto the field.

They win by:

• setting the vision

• building a system

• motivating people

• getting the right players

• refining their skills

• putting those players in the right spot at the right time

The first step in doing a new job is to understand it!

(Not sure what the job is? Use Tactical Items to clarify.👇)

From Founder to CEO: Tactical Items

As James Clear says:

Every action is a vote for the type of person you wish to become.

Become the CEO by doing things that CEOs do. Here are specific strategies to uplevel.

1. Make time for personal development.

Every founder who is serious about getting their company to the next level spends time learning.

You can do it many ways:

• Peer groups

• Podcasts, books, blogs, stories

• Coaching

CEOs are busy but they find the time to get better and ways to create accountability for themselves.

2. Learn from people smarter than you.

How do you figure out what the CEO job is?

• Work with an executive coach or peer group

• Talk to your advisors, mentors, or investors

• Ask founders who are a stage or two ahead of you

Successful founders are always getting insight from others with different perspectives or more experience.

3. Vision, strategy, goals.

The team is looking to you for guidance.

It needs to be consistent and well-communicated.

(Start with a Weekly Update if you’re not doing it already!)

Time to get clear and (over) communicate about:

• Priorities

• Goals (← new fave post about goals)

• Strategy - via One Page Strategic Plan

• Elevator Pitch

4. Do a productivity audit.

Feeling too busy to learn? Don’t have time to work on strategic items?

A simple starting place: conduct a productivity audit!

See what you are doing every week that could be delegated, eliminated, combined, moved to email, adjusted to monthly, or otherwise streamlined.

You get:

1. More time

2. Insight about what you (and others) are working on

I have never done this without finding several “ah-ha” moments of things I can cancel, quit, or deprioritize.

5. Delegate!

Hand off specific tasks.

Clarify when someone can make a decision on their own.

Offer others opportunities to grow.

Give away your Legos!

These are all mission critical to a healthy company and effective CEO leadership.

Here’s my favorite framework and a gentle reminder: don’t be a bottleneck!!

6. Go on vacation.

This is not a joke. I mean it.

The best way to get out of the weeds is to be gone for a while and watch how awesome your team does without you!

If you’re not ready for this step, start by not replying.

Seriously.

Let your team know that you’ll be slower replying to emails and chats.

Now, watch with amazement how much people can figure out when you’re not available!

It’s like my kids who can magically tie their own shoes and get their own snacks when I’m not around. CEO MODE!!!!!

How did you develop your leadership skills as your company grew? What was the hardest part for you? Any other tips??

• Mark Suster

• David Cummings

David was the CEO and co-founder of Pardot. (But that wasn’t the only reason I read his blog, okay??!!!)

The dude was building multiple successful startups and ALSO blogging every single day including weekends.

Also, his posts are like 100 words so if you find my style a tiny bit too verbose, you’re in for a (short) treat!

He still posts every Saturday so if you’re not subscribed, fix that (bottom right corner)!

David’s blog is thousands of posts of startup gems that I still reference regularly.

Want the Cliff Notes AI summary?

Here are the topics and specific posts that I share most often with founders!

1. Partnerships

Will that partnership unlock millions of revenue for your startup?

Here are the posts I send founders who are excited about a possible partnership.

(Sorry in advance for the buzzkill! 😬 Paul Graham says the same thing in the “Big” section here.)

Read one:

• Startups Should Say No to 99% of Partnership Opportunities

Read more:

• Walk, Jog, Run Approach to Partnerships

• 4 Reasons for Startups to Avoid Big Partnerships

• Purposefully Adding Friction to a Process

2. Rule of 40

If you don’t know the Rule of 40, you should! And here’s your chance to learn.

It’s a great way to answer the question: what’s more important — growth or profitability?

Read one:

• Rule of 40 and Startups (Dec 2019)

Read more:

• SaaS Valuations as a Rule of 40 Multiple (Jul 2020)

• Back to the Rule of 40 for Startups (Jun 2022)

• Startup Valuations as Rule of 40 and Market Sentiment Multiples (Jan 2023)

• Rule of 40 Growth Multiplier (Feb 2023)

3. Culture

Culture is the only sustainable competitive advantage that’s completely within the entrepreneur’s control. - David Cummings

^^Can confirm! I saw it first hand at Pardot.

Our culture directly impacted our successful outcome. Customers felt it and it created loyalty. It also made us an attractive acquisition target. Exact Target and Salesforce both mentioned it in the acquisition process!

Read one:

• 12 Ideas To Strengthen Culture (👈 includes links to posts about each idea)

Read more:

• Core Values for Atlanta Tech Village

• Culture Deck in Time of Crisis

4. Origin Stories

Get inspired and see behind the scenes how a legendary entrepreneur thinks about business ideas and tells the stories!

Read one:

• Intown Golf Club’s Origin Story (Aug 2024)

Read more:

• The Perlant Grand Opening (Jan 2025)

• From Historic Neighborhood to Startup District in Downtown Atlanta (Aug 2024)

• New Atlanta Tech Village in Downtown Atlanta (Jul 2024)

• Salesloft Partnered With Vista Equity (Dec 2021)

5. Find New Business Ideas

How do you find a great business idea?

Listen to the person who is great at coming up with billion dollar business ideas!

For example, David wrote the original post on Authentic Demand which I’ve talked about here, here, and here.

And that’s just the beginning. I share these tips on finding ideas every week!

Read one:

• 5 Favorite General Tips For Founders

Read more:

• The 1 Question to Ask When Looking for a Startup Idea

• 4 Quick Ways to Evaluate a Startup Idea as an Investor

• Get Started on an Idea

• Finding a Startup Idea

• Seeking Startup Ideas

If you’re a David Cummings blog reader, what’s your favorite post or topic? Do you have blog posts that you regularly reference or share?

LOLOLOLOL.

Never gets old. #momjoke

Mostly I’m just trying to:

• load my kids up with veggies

• get them a good night’s sleep

• lean on my husband for everything else (thanks, Kyle!!!!!! 😘)

Our kids are 6 and 8 years old, so while they’re not yet using AI agents to start their own companies, we are intentionally introducing some financial and entrepreneurial concepts.

I’ll update this post in 20 years to let you know how we did. 😆

Here are the 5 money lessons we’re teaching our kids, based on what I’ve heard talking to founders, experienced in my own life, and learned from people smarter than me!

5 Money Lessons I’m Teaching My Kids

1. Talk about money

The first rule about money is…talk about money!

(Opposite of Fight Club 😉)

Financial literacy starts starts by making it okay and normal to talk about money!

Treat money like a:

• tool

• resource

• topic for learning

Money is NOT:

• taboo

• secret

• only for adults or rich people

I will forever be on my soapbox for founders to lead with money when talking to VCs and for women to be encouraged to talk openly about money (salaries, negotiations, strategies, deal terms).

I think it’s true for kids too.

Some parents want to “protect” kids from the stress of money.

I totally understand that but I’ve also seen it backfire when those kids get into debt or make poor financial choices because of lack of knowledge.

When you discuss money (in an age-appropriate way), you prepare and empower kids!

2. Save 50%

When our kids started getting Tooth Fairy and birthday money, a big question came up:

How much do you need to save vs. spend?

We held a family meeting to discuss.

We talked about why saving was important:

• Saving gives you options.

• Decreases stress when emergencies happen.

• Enables job flexibility.

• Lets you do things like travel and start companies. 😉

Our kids suggested 50% savings rate. Boom! Done.

Now, with any “income,” we transfer half into their bank account and show them on our phone.

The rest is available for them to spend on what they want.

Pokemon cards, golf tees, and activity books of course.

One of the saddest conversations I have is when someone would love to start a company, but their lifestyle is too expensive to make a change.

I’ve known other founders who have given themselves second and third startup lives because their living expenses were low and savings robust.

Of course, you can’t always do this. Maybe you have dependents or you’re paying off student loans.

But keeping lifestyle inflation in check will always serve you.

Save lots and live within your means to give yourself maximum flexibility as a founder and beyond!

3. Want more money? Start a business.

Occasionally our kids will want to buy something more expensive or generally “want more money.”

We say: “Great! Let’s talk about how to start a business.”

• Ask neighbors about their problems.

• Things like:

  • Taking out the trash

  • Picking up dog 💩

  • Yard work

So far, the desire for “more money” has quickly faded when our kids hear they need to talk to an adult. 😂

We have had some successful forays into online selling:

• Our kids cleaned the old double stroller and got a % of the online sale.

• One child sold toys on Facebook Marketplace to learn about value arbitrage and the circular economy! (That’s what he learned, right? I keep telling myself that. 😉)

I’ve seen the “flyers” made by great founders when they were kids. Hustling from an early age!

4. Work is not only about money.

Possibly controversial. We don’t pay for chores.

(Here’s our chore system.)

Everyone must pitch in. It’s part of being a family and running a household. It takes work and everyone contributes.

We do this for several reasons:

• Parental sanity. Kids can do more than you think and it helps the daily grind when kids do chores! The reminders and debates are annoying. But I like that I’m not doing all the work solo. I’d rather nag them now than later.

• Independence and overall life satisfaction. Research shows that doing chores is great for kids’ confidence, resilience, making friends, being healthier, academic performance, and just about everything. So yeah. We’re doing chores.

• Learn the joy of a job well done. While great founders love to make money, they also have a great work ethic. Most success comes from giving first, doing the right things, and putting in work without knowing the specific payoff.

• Be part of a team and understand collaboration. Every now and then, our kids will get fired up and actually help each other with chores. And even when they’re complaining or bickering (aka most of the time), they are still gonna learn teamwork dammit!

5. Ask for what you want (and how you ask matters!)

Not a money lesson per se, but very related.

The best founders and most successful people ask for what they want.

If you don’t ask, the answer is always no.

^^one of my favorite blogs of all time. Adam Blitzer shared it with me in the early days of Pardot and it stuck with me 15 years later!

Most things are possible — but you have to ask and you need to ask in a way that make people want to help you.

“THAT’S NO FAIR, I WANT A COOKIE!” is usually not as effective as, “That cookie looks delicious. Would I be able to have one please?”

And you’d be surprised at how many adults still use, “That’s not fair” as a way to ask for something. 😆

Kid Examples:

• Our kids order their own food at restaurants

• They call their grandparents to ask questions (e.g. can I borrow this book?)

• They need to ask when they want to join a playground game, get free sprinkles, or anything else!

How do you get invited to a key event, solicit a customer testimonial, meet the CEO, and generally do things that grow your company and build wealth?

You need to ask.

And how do you get repeat invites, testimonials, and intros?

You need to be really appreciative and grateful so people help you again!

What’s your best money advice? What are you teaching kids about money? If you have adult kids, what worked and what would you do differently? I’d love to hear!