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May 5, 2017 · 23m · 20vc

20VC: Why We Are Still In The Very Early Days For Fintech, Why Your Company Has To Have An Opinionated Culture & Why The CEO Should Not Be The Sole Point Of Contact With The Board with Bill Clerico, Founder & CEO @ WePay

Bill Clerico · 15m spoken Harry Stebbings · 7m 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 episode of The 20 Minute VC, host Harry Stebbings interviews Bill Clerico, Co-founder and CEO of WePay, discussing his startup journey, fundraising resilience, company culture, board governance, and the evolving fintech landscape. Clerico provides key insights into executing high-stakes business pivots, fostering investor trust, and making crucial early executive hires.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 33.6% of the talking time here. How this is scored →

Harry as informed peer 2.8 Guest teaching 5.0 Guest disagreement 1.8 Harry pushing back 2.0
05100:0010:0020:002:32–8:49 · Harry as informed peer 2/10 Bill Clerico's Background and the Origins of WePay Harry asks conversational questions about Bill's background and fundraising experience. Bill reframes the idea that capital is a commodity, explaining that strong investor relationships are critical when a company goes through rough patches.8:49–13:14 · Harry as informed peer 3/10 Defining and Evolving an Opinionated Company Culture Harry pushes past generic culture buzzwords by citing Brad Feld and asking for concrete examples of a contrarian culture. Bill explains culture as implicit behavioral guidelines when nobody is watching, citing WePay's practice of investing in relationships.13:14–17:17 · Harry as informed peer 3/10 Managing Pivots and Scaling Board Communication Harry prompts Bill on how WePay navigated a major pivot that wiped out 70% of revenue. Bill dismantles the friendly Silicon Valley euphemism of a pivot, explaining that it fundamentally means the founder was wrong and failed on their initial strategy.17:17–21:45 · Harry as informed peer 3/10 The Strategic Importance of an Early CFO Hire Harry cites industry trends showing many unicorn startups pre-IPO lack CFOs before moving into a rapid quickfire round. Bill educates on why payments companies need financial leadership early and how CFOs offer an unbiased perspective on internal capital allocation.2:32–8:49 · Guest teaching 5/10 Bill Clerico's Background and the Origins of WePay Harry asks conversational questions about Bill's background and fundraising experience. Bill reframes the idea that capital is a commodity, explaining that strong investor relationships are critical when a company goes through rough patches.8:49–13:14 · Guest teaching 5/10 Defining and Evolving an Opinionated Company Culture Harry pushes past generic culture buzzwords by citing Brad Feld and asking for concrete examples of a contrarian culture. Bill explains culture as implicit behavioral guidelines when nobody is watching, citing WePay's practice of investing in relationships.13:14–17:17 · Guest teaching 6/10 Managing Pivots and Scaling Board Communication Harry prompts Bill on how WePay navigated a major pivot that wiped out 70% of revenue. Bill dismantles the friendly Silicon Valley euphemism of a pivot, explaining that it fundamentally means the founder was wrong and failed on their initial strategy.17:17–21:45 · Guest teaching 4/10 The Strategic Importance of an Early CFO Hire Harry cites industry trends showing many unicorn startups pre-IPO lack CFOs before moving into a rapid quickfire round. Bill educates on why payments companies need financial leadership early and how CFOs offer an unbiased perspective on internal capital allocation.2:32–8:49 · Guest disagreement 2/10 Bill Clerico's Background and the Origins of WePay Harry asks conversational questions about Bill's background and fundraising experience. Bill reframes the idea that capital is a commodity, explaining that strong investor relationships are critical when a company goes through rough patches.8:49–13:14 · Guest disagreement 1/10 Defining and Evolving an Opinionated Company Culture Harry pushes past generic culture buzzwords by citing Brad Feld and asking for concrete examples of a contrarian culture. Bill explains culture as implicit behavioral guidelines when nobody is watching, citing WePay's practice of investing in relationships.13:14–17:17 · Guest disagreement 3/10 Managing Pivots and Scaling Board Communication Harry prompts Bill on how WePay navigated a major pivot that wiped out 70% of revenue. Bill dismantles the friendly Silicon Valley euphemism of a pivot, explaining that it fundamentally means the founder was wrong and failed on their initial strategy.17:17–21:45 · Guest disagreement 1/10 The Strategic Importance of an Early CFO Hire Harry cites industry trends showing many unicorn startups pre-IPO lack CFOs before moving into a rapid quickfire round. Bill educates on why payments companies need financial leadership early and how CFOs offer an unbiased perspective on internal capital allocation.2:32–8:49 · Harry pushing back 1/10 Bill Clerico's Background and the Origins of WePay Harry asks conversational questions about Bill's background and fundraising experience. Bill reframes the idea that capital is a commodity, explaining that strong investor relationships are critical when a company goes through rough patches.8:49–13:14 · Harry pushing back 4/10 Defining and Evolving an Opinionated Company Culture Harry pushes past generic culture buzzwords by citing Brad Feld and asking for concrete examples of a contrarian culture. Bill explains culture as implicit behavioral guidelines when nobody is watching, citing WePay's practice of investing in relationships.13:14–17:17 · Harry pushing back 2/10 Managing Pivots and Scaling Board Communication Harry prompts Bill on how WePay navigated a major pivot that wiped out 70% of revenue. Bill dismantles the friendly Silicon Valley euphemism of a pivot, explaining that it fundamentally means the founder was wrong and failed on their initial strategy.17:17–21:45 · Harry pushing back 1/10 The Strategic Importance of an Early CFO Hire Harry cites industry trends showing many unicorn startups pre-IPO lack CFOs before moving into a rapid quickfire round. Bill educates on why payments companies need financial leadership early and how CFOs offer an unbiased perspective on internal capital allocation.

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

0:00 · Harry 93.6% · guest 6.4%0:00 · Harry 93.6% · guest 6.4%3:00 · Harry 21.7% · guest 78.3%3:00 · Harry 21.7% · guest 78.3%6:00 · Harry 16.1% · guest 83.9%6:00 · Harry 16.1% · guest 83.9%9:00 · Harry 15.2% · guest 84.8%9:00 · Harry 15.2% · guest 84.8%12:00 · Harry 14.5% · guest 85.5%12:00 · Harry 14.5% · guest 85.5%15:00 · Harry 18.7% · guest 81.3%15:00 · Harry 18.7% · guest 81.3%18:00 · Harry 12.3% · guest 87.7%18:00 · Harry 12.3% · guest 87.7%21:00 · Harry 79.7% · guest 20.3%21:00 · Harry 79.7% · guest 20.3%
Sharpest disagreement ▶ 13:34 Pivoting Means You Failed

Bill rejects the friendly Silicon Valley catch-all framing of a pivot, stating bluntly that it simply means an entrepreneur failed on their original product hypothesis.

 Hardest push from Harry ▶ 10:34 Challenging Fluffy Culture Definitions

Harry refuses to settle for generic cultural buzzwords like teamwork or kindness, challenging Bill to define what an actual contrarian or opinionated culture looks like.

 Biggest teaching moment ▶ 5:39 Capital is Not a Commodity in Tough Times

Bill corrects the common narrative that venture capital is purely commoditized, explaining that deep relationship trust with investors is the only thing that keeps a company alive when strategy goes sideways.

 Harry holds his own ▶ 17:17 Citing Pre-IPO Unicorn CFO Trends

Harry demonstrates domain research by pointing out that many high-profile unicorn startups operate pre-IPO without a formal CFO, pressing Bill to justify hiring one early.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Bill Clerico's Background and the Origins of WePay 2521 Harry asks conversational questions about Bill's background and fundraising experience. Bill reframes the idea that capital is a commodity, explaining that strong investor relationships are critical when a company goes through rough patches.
Defining and Evolving an Opinionated Company Culture 3514 Harry pushes past generic culture buzzwords by citing Brad Feld and asking for concrete examples of a contrarian culture. Bill explains culture as implicit behavioral guidelines when nobody is watching, citing WePay's practice of investing in relationships.
Managing Pivots and Scaling Board Communication 3632 Harry prompts Bill on how WePay navigated a major pivot that wiped out 70% of revenue. Bill dismantles the friendly Silicon Valley euphemism of a pivot, explaining that it fundamentally means the founder was wrong and failed on their initial strategy.
The Strategic Importance of an Early CFO Hire 3411 Harry cites industry trends showing many unicorn startups pre-IPO lack CFOs before moving into a rapid quickfire round. Bill educates on why payments companies need financial leadership early and how CFOs offer an unbiased perspective on internal capital allocation.

Statements from this episode (10)

Assertion Not checkable as stated
Bill Clerico pitched 40 Boston VCs before YC without raising funds
“I think I pitched four DVCs in Boston and, you know, didn't raise a dime.”
Bill Clerico May 5, 2017 ▶ 5:14
Insight
Clerico: Great founders are transparent with investors about challenges
“I think what sets apart great entrepreneurs from not so great entrepreneurs are the ones that can be honest and candid about those challenges and enlist their investors help and keep them in the loop on that.”
Bill Clerico May 5, 2017 ▶ 7:40
Insight
Clerico: One bad investor on a cap table can ruin a startup
“One bad apple on your cap table can really spoil or even ruin the company.”
Bill Clerico May 5, 2017 ▶ 8:38
Insight
Clerico: Culture is the set of norms guiding unmonitored employee behavior
“What culture is, is it's the set of, kind of, norms and guidelines that guide people's behavior when no one's telling them what to do, and I think that, As a tool is incredibly powerful. You know, if as a leader, you can set a set of guidelines and values and …”
Bill Clerico May 5, 2017 ▶ 9:11
Insight
Clerico: Great companies require an opinionated culture with explicit stances
“I think great companies have an opinionated culture. It's not just sort of generic. There's specific stances that they take Terms of values, norms, behaviors that help dictate that common set of behavior.”
Bill Clerico May 5, 2017 ▶ 9:48
Insight
Clerico: A Startup Pivot Means You Failed as an Entrepreneur
“We in Silicon Valley use this term pivot as this catch-all Friendly term to just say, Hey, we're going to change our business strategy. But what it actually means is that you've failed as an entrepreneur. You know, you've, your strategy, your mission, your obj…”
Bill Clerico May 5, 2017 ▶ 13:35
Insight
Clerico: CEOs Should Not Be the Sole Board Contact as Companies Scale
“I think it's also important to, as you grow as an entrepreneur, to not be the sole point of contact with your board. You know, you have a management team, you have a CFO. Making sure that you're bringing your team into those board meetings, helping your team d…”
Bill Clerico May 5, 2017 ▶ 16:27
Insight
Clerico: CFOs are the only role providing unbiased, cross-company evaluation
“And I think the other sort of unspoken benefit of CFOs is that they're really the only other function that can look across the entire company in an unbiased way and help sort of measure performance and help advise the CEO on how to invest the company's resourc…”
Bill Clerico May 5, 2017 ▶ 17:56
Assertion Not checkable as stated
Bill Clerico: Big Banks Remain Unaffected by Fintech Disruption
“The reality is that the big banks have really been unaffected by fintech. You know, fintech has yet to really disrupt major parts of the market, and so I think it's still very, very early days, and it'll be exciting to watch what fintech does over the next 10 …”
Bill Clerico May 5, 2017 ▶ 20:30
Prediction Partly held up
Bill Clerico: WePay Will Expand Internationally and Into Lending and Insurance
“You know, we think that there's a huge opportunity in international expansion. That'll be a big priority for us. The other thing too is we think there's opportunity outside of peer payments. So today we pay as a payments company, but we think that over time th…”
Bill Clerico May 5, 2017 ▶ 21:16
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