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How to bet on yourself (without venture capital)

How to bet on yourself (without venture capital)

21 segments available

William Hockey, co-founder of Plaid and founder of Column, joins the show to discuss building the global operating system for the US dollar. Unlike the typical Silicon Valley playbook, William funded Column entirely with his own to avoid the "hamster wheel" of venture capital. In this conversation, he shares unconventional wisdom on why modern founders take too little risk, the strategic importance of solving boring problems, and why he spends time in emerging markets like Kinshasa. We also cover the US dollar as a national security asset and why distribution will matter more than technology in the AI era. Timestamps: 0:00 Intro 9:19 Emerging Markets 14:03 Silicon Valley's Elite Consensus Problem 16:03 Rejecting the VC Hamster Wheel 21:45 Equity and Liquidity 26:03 Funding a Bank 29:45 The Necessity of Extreme Founder Risk 37:18 Finding Leverage 45:20 Longevity and Profitability in Banking 48:46 Matching Your Capital Structure to Your Business 51:44 The Unseen Power of the US Dollar 1:02:30 How AI Will Transform Legacy Banks 1:09:23 The Kindest Thing #investing #business #founder #fintech #banking #startups #siliconvalley #risk #entrepreneurship #finance Presented by Ramp: https://ramp.com/invest Sponsored by Vanta, WorkOS, Rogo, and Ridgeline: https://www.vanta.com/invest https://workos.com/ https://rogo.ai/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc

Segments Timeline

1
0:00 - 1:30
1:30 duration269 words

Introduction to William Hockey and Column

An introduction to William Hockey, his journey through fintech, and a glimpse into what makes his insights valuable.

"My guest today is William Hockey, the founder of Column. William was also the co-founder of Plat, one of the more famous fintech businesses from the last decade. Column is his second business, which h..."

2
1:30 - 4:31
3:01 duration576 words

Understanding Column's Business Model

William Hockey explains Column's unique business model, integrating banking and software services.

">> Can you just start by explaining what the business is and does at a high level? We are a software company that also owns a bank. And what we do is we say, okay, we have this interesting regulatory ..."

3
4:31 - 7:35
3:04 duration689 words

Exploring Global Markets and Constraints

William discusses the importance of understanding global markets and the unique opportunities in constrained societies.

"One of the things I love whenever we talk is you've always been somewhere strange and interesting. Kinshasa, I think, was the last time we were together. I don't know a lot of founders going to Kensha..."

4
7:35 - 13:40
6:05 duration1319 words

Experiences in Kinshasa

William talks about his experiences in Kinshasa and the insights gained from interacting with local entrepreneurs.

"so sticking with Kinshasa as an example so you go there what are you doing there what are you discovering say more about like this con the constraints you encounter there like teach us a bit about I'v..."

5
13:40 - 16:45
3:05 duration722 words

Consequences of Silicon Valley's Consensus Culture

William discusses the consequences of Silicon Valley's consensus-driven culture and its implications for innovation.

"Do you end up earning similar amounts of revenue from outside the US as you do inside because of these potential relationships? the US market is so good and and fintech is so developed and and I do th..."

6
16:45 - 21:18
4:33 duration523 words

Innovating Without Venture Capital

William Hockey shares insights on building a company without relying on venture capital funding.

"Most software companies try to maximize your time on their app to juice engagement. RAMP does the exact opposite. RAMP understands that no one wants to spend hours chasing receipts, reviewing expense ..."

7
21:18 - 22:49
1:31 duration465 words

Long-Term Thinking in Business

William emphasizes the importance of long-term thinking and decision-making in building Column.

"I think yes, Silicon Valley companies are probably like more long-term oriented than your average business in the US, but I think the hamster wheel of VC doesn't actually allow us to be long-term beca..."

8
22:49 - 24:19
1:30 duration439 words

Unique Cultural and Financial Practices at Column

William discusses the unique practices he's implemented at Column, focusing on employee ownership and long-term investment.

"I mean, like like we bought a regulated bank when we were early. I think that's like, you know, it's probably like a little bit cooler now in this new administration, but we bought a regulated bank du..."

9
24:19 - 25:50
1:31 duration361 words

Employee Communication and Retention Strategies

William shares how he effectively communicates ownership and retention strategies to employees at Column.

"That's a really good example maybe just to pull it apart a bit more. Are you vest are you granting equity to people in a similar way that a normal startup would vesting over some period of time and th..."

10
25:50 - 27:21
1:31 duration319 words

Addressing Employee Needs Beyond Financial Gain

William reflects on employee motivations and the workplace culture at Column.

"How have you honed the communication of that idea to a new employee so that they get it? Because I think so often people just say, "Oh, I got this many shares and like this is the, you know, this is t..."

11
27:21 - 28:52
1:31 duration358 words

Differentiating Employee Experiences at Column

William discusses the practices that make Column unique for employees compared to typical Silicon Valley startups.

"Does this empirically show up in employee retention numbers versus like Silicon Valley norms? we have almost almost close to no no regretted attrition which means kind of people that we like to stay e..."

12
28:52 - 30:22
1:30 duration410 words

The Burden of Startup Risks

William reflects on the burdens and risks associated with running a startup, particularly focusing on founder responsibilities.

"That resonates with a certain type of person, but it doesn't resonate with everybody. And so building a company, building a culture that actually optimizes for every single point of an employes journe..."

13
30:22 - 31:52
1:30 duration267 words

Navigating Financial Stress as a Founder

William opens up about the stress and challenges of managing finances while building Column.

"Talk about that stress. Like, you got to like let us in the room on that. The first three years were definitely the most stress of my life because I I had a fundamental thesis that we could pull this ..."

14
31:52 - 34:54
3:02 duration376 words

Psychological Impact of Entrepreneurial Risks

William reflects on the transformative psychological impact of taking extreme entrepreneurial risks.

"I think that the good founders bet on themselves and take an extreme amount of risk to do that. And I think the extreme amount of risk part is something that we no longer have. But when like when ther..."

15
34:54 - 37:55
3:01 duration535 words

Changes in Perspective Over Time

William shares how his experiences as a founder have shifted his perspectives and motivations over time.

"I always am somewhat perplexed by, you know, like I'm a second time founder, but I'm not alone. Like there's a lot of great founders I shall not name that, you know, have made a bunch of money. And yo..."

16
37:55 - 39:26
1:31 duration631 words

Reflection on Personal Investment and Motivation

William concludes with a reflection on his personal investment in Column and the driving forces behind his entrepreneurial journey.

"Yeah. And it's caused a lot of companies to be just super safe companies like hey we're going to like pivot to AI and like wrap open AI wrap anthropic whatever like that's not bold that's not ambitiou..."

17
39:26 - 40:58
1:32 duration116 words

Value of Deep Study

Insights on the value derived from extensive reading and how small findings can translate into significant business value.

"What's something not necessarily that book, but like what's something you get out of that degree of extreme study? >> The hard part about this is you probably get like one small thing in a 20,000page ..."

18
40:58 - 43:59
3:01 duration148 words

Finding Value in the Boring

Exploring how passion for seemingly mundane subjects can provide advantages in entrepreneurship.

"So, what have you learned about how to become apart from reading, you know, obscure 19th century Chinese banking books? Like, what else have you learned about how to become the best in the world at wh..."

19
43:59 - 1:02:12
18:13 duration125 words

Insights on Picking Talent

How past experiences shape the approach to hiring and what traits to look for in potential employees.

"What about picking talent? Like how how what things do you optimize for now that uh have been honed because of your prior experience? I >> mean people always think about employees and it's like like a..."

20
1:02:12 - 1:12:48
10:36 duration121 words

Future of Financial Services

Highlighting ambitions for the future of financial services and the importance of retaining power in the US.

"I still hope it's very USbound >> and I think we sometimes want to believe this world where um there's a lot of people in Silicon Valley that I fundamentally disagree with that want to put the power o..."

21
1:12:48 - 1:13:33
0:45 duration87 words

Kindness and Resilience

Reflecting on personal life lessons and the importance of resilience taught through childhood experiences.

"I've had a lot of kind people in my life, but I think it's challenging to to not look back and be like, "Oh, like your mom and dad were like the kindest people." Um, my mom and dad did not have um hav..."