5 Lessons From 5 Years at Atlanta Ventures

Kathryn O'Day

Apr 14, 2026

Time flies when you’re having fun.

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??