Mar 3, 2023 · 17m · top-founders

How This Angel Investor Got $20k Check into Cloudability, 40% Checks Still in Play

Ben Kepes · 11m spoken Nathan Latka · 4m spoken

0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this interview with Nathan Latka, veteran angel investor and board director Ben Kepes shares his framework for early-stage B2B SaaS investing, startup board governance, portfolio risk management, and founder dynamics.

Chapters · click to jump

1 statement ▾

Ben Kepes Was Cloudability's First Investor, Introduced Founders to Foundry Group open →

1 statement ▾

CEOs Cannot Be Completely Honest With Employees, Must Rely on Boards open →

1 statement ▾

Founders Sometimes Cut Off Angel Investors After Raising Institutional Rounds, Kepes Says open →

4 statements ▾

Ben Kepes's Initial Angel Check Into Cloudability Was $20,000 To $30,000 open →

Ben Kepes Avoids Angel Networks Because They Are 'Kind of Douchebaggy' open →

60% of Kepes's Realized Angel Investments Yielded Positive Returns, 40% Went Zero open →

Angels Should View Invested Capital as Payment for the Experience open →

1 statement ▾

Work-Life Balance Is Impossible for Scaling SaaS Founders, Kepes Argues open →

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 29.1% of the talking time here. How this is scored →

Nathan as informed peer 5.4 Guest teaching 3.2 Guest disagreement 1.8 Nathan pushing back 3.4

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

Sharpest disagreement ▶ 14:44 Pyrrhic victory of retaining founder board control

Kepes rejects Nathan's framing that founders should engineer term sheets to protect themselves from termination, arguing that holding onto a CEO role through legal tricks hurts the company.

Hardest push from Nathan ▶ 10:05 Nathan demands clarity on portfolio returns

Nathan refuses vague answers about investment performance, pressing Kepes to clarify whether a positive outcome merely meant returning capital or achieving significant multiples.

Biggest teaching moment ▶ 15:14 Schooling on founder skill evolution and exit readiness

Kepes educates listeners and the host on governance realities, explaining that very few founders possess the skill sets to take a company from early seed all the way through an IPO.

Nathan holds their own ▶ 13:54 Nathan breaks down Series A common stock board traps

Nathan demonstrates advanced venture knowledge by explaining the contractual vulnerability when board appointment rights are assigned to majority of common rather than the founder by name.

the scores for every segment, with the reasoning behind each

Topic	Nathan as informed peer	Guest teaching	Guest disagreement	Nathan pushing back	Why
Evaluating B2B SaaS Investments and the Swiped On Story	5	2	1	3	Nathan pulls up specific background data on Swiped On's $700k NZ funding round and queries Kepes's vehicle Diversity.net.nz. Kepes calmly clarifies his personal angel participation alongside New Zealand's co-investment fund.
Early Angel Bets in Cloudability and Siftery	5	3	1	2	Nathan demonstrates domain knowledge by citing Cloudability's $20M revenue milestone and historical funding numbers before asking about board dynamics. Kepes details the difference between governance and management, sharing a story about navigating an outsourced developer crisis.
Founder-Investor Dynamics Across Venture Funding Stages	6	3	2	5	Nathan drills into Kepes's angel portfolio track record, demanding precise win-loss ratios and challenging what qualifies as a positive outcome. Kepes acknowledges the reality of early angel checks going silent after subsequent institutional rounds.
Hidden Exits, Missed Unicorns, and the Multi-Project Lifestyle	4	2	1	2	Nathan asks about missed opportunities like Canva and whether Kepes has an itch to build a full-time SaaS company. Kepes explains why he prefers holding a diverse portfolio of board seats and manufacturing assets over the grueling startup founder lifestyle.
Series A Board Structures, Control Rights, and CEO Transitions	7	6	4	5	Nathan presents a detailed technical scenario regarding Series A board seat allocations tied to majority of common versus named individuals. Kepes counters by arguing that obsessing over legal mechanics to preserve founder control is often a pyrrhic victory if the founder is no longer the right fit to scale the business.

Statements from this episode (8)

Disclosure

Ben Kepes Was Cloudability's First Investor, Introduced Founders to Foundry Group

“So I was the first first investor in Cloudability. And again, that was super interesting. Invested introduced those guys to Brad and the team at the Foundry you know, watch that investment play out over time. And then they got, got acquired by Aptio.”

Ben Kepes Mar 3, 2023 ▶ 4:18

Insight

CEOs Cannot Be Completely Honest With Employees, Must Rely on Boards

“The reality is a C it's super hard because you can't be completely honest with your employees because, you know, at the end of the day, the buck stops with you. And so, Your board members, you should absolutely see them as a sounding board that you can be tota…”

Ben Kepes Mar 3, 2023 ▶ 7:12

Disclosure

Founders Sometimes Cut Off Angel Investors After Raising Institutional Rounds, Kepes Says

“I mean, I've had not with CloudAbility, but with other companies, I've had sort of the email from CE saying, hey, we've done Series A, B, C, whatever from now on, we probably won't be updating you ever, and I won't reply to your emails, kind of thing, which is…”

Ben Kepes Mar 3, 2023 ▶ 7:52

Disclosure

Ben Kepes's Initial Angel Check Into Cloudability Was $20,000 To $30,000

“I mean, the chick size was, from memory, it was like, 20, 30 k, so not much at all.”

Ben Kepes Mar 3, 2023 ▶ 9:07

Opinion

Ben Kepes Avoids Angel Networks Because They Are 'Kind of Douchebaggy'

“So, you know, one option is to get involved in an angel network. I'm not so big on that because it's kind of douchebaggy.”

Ben Kepes Mar 3, 2023 ▶ 9:26

Disclosure

60% of Kepes's Realized Angel Investments Yielded Positive Returns, 40% Went Zero

“So there's probably 40% still in play. I would say I've been super lucky. So probably 60% of the ones that have had an outcome have been a positive outcome. 40% have been to zero.”

Ben Kepes Mar 3, 2023 ▶ 10:07

Insight

Angels Should View Invested Capital as Payment for the Experience

“For an angel, don't invest anything you're not prepared to lose. When you do invest, really enjoy the ride, but you, you're kind of paying for the ride, and if you have an outcome at the other end, that's a bonus, and so I don't think about that money.”

Ben Kepes Mar 3, 2023 ▶ 11:21

Insight

Work-Life Balance Is Impossible for Scaling SaaS Founders, Kepes Argues

“And the reality is that as a SaaS founder, no matter what people say, you don't have that balance because you have to focus because it's a short life cycle. And in order to scale to the level, To see the outcome you need to be hustling.”

Ben Kepes Mar 3, 2023 ▶ 13:39

How This Angel Investor Got $20k Check into Cloudability, 40% Checks Still in Play

How this conversation actually went

Statements from this episode (8)

Turn any episode into a week of clips.