Why Founders Feel Lost After a Successful Exit - Barak Kaufman - Post-Exit Founders - EP#117

When you sell your company and hit the milestone most founders only dream of, why does it feel so lonely?

Barak Kaufman has met around 2,000 exited founders, and almost all of them describe the same thing.

In this episode of Not Another CEO Podcast, I sat down with Barak Kaufman, an investor, operator, exited founder and community builder.

Barak started his career at Insight Partners, co-founded Intello (Which competed with my company, BetterCloud), and sold it to SailPoint in 2021. He then started Post-Exit Founders, now more than 7,000 members across 12 countries. Today he is a partner at Vine Ventures and Chief Strategy Officer at Wonderful, an applied AI company.

We cover identity loss after an exit, building in the AI era, startup life in New York and Israel, and what founders get wrong about investors.

Takeaways

1. The hardest part of an exit is identity, not money: Barak says most exited founders feel lost and lonely, and many end up with a boss for the first time in years.

2. Take a year off and commit to nothing: His advice is 12 months, not six and not 24. The biggest mistake he sees is jumping into the next company because the in-between phase is uncomfortable.

3. Luck and agency both matter: Exited founders split on whether they got lucky or slaved for it. Barak believes in agency and says the founders he respects most don’t blame the situation.

4. Building in the AI era is faster, but the fundamentals haven’t changed: Wonderful’s deals are mostly over $1M a year, versus about $30K at Intello. A-plus talent, enablement and enterprise trust still decide who wins.

5. Believe your pitch: Barak admits he’s not sure he truly believed his own billion-dollar story at Intello. His standard for founders is believing that you will get there, not that you can.

6. Run your fundraise like a process: Most VCs have less figured out than founders think, and FOMO drives a lot of decisions. Be tactical, not passive.

Quote of the Show

“When you build a company and you sell that company and you reach the milestone that many would only dream of, it ends up feeling very weird and very lonely.” - Barak Kaufman, Chief Strategy Officer, Wonderful

Guest Featured in this Episode: Barak Kaufman, Chief Strategy Officer, Wonderful
LinkedIn: https://www.linkedin.com/in/barakk/

Post-Exit Founders: https://pef.co/

Vine Ventures: https://vineventures.com/

Wonderful: https://www.wonderful.ai/

We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.

Chapters:

00:00 Trailer & Introduction
02:47 From investor to founder to Wonderful's Chief Strategy Officer
04:46 What Wonderful does and how it started
07:37 Building in the SaaS era vs. the AI era
11:07 What stays the same: talent, enablement and enterprise sales
17:44 Inside Post-Exit Founders: the identity loss after an exit
22:30 Take a year off, and the paths after an exit
30:28 Why everyone wants to be a founder
34:06 Luck, skill and what sets exited founders apart
38:05 Agency over timing: Airtable, Miro and COVID
44:29 New York vs. Israel startup ecosystems
48:01 Inside Israel's talent war
51:14 What founders don't understand about investors
57:53 FOMO, hot rounds and the flight to quality
1:00:02 The advice he'd give his younger self