Mar 31, 2023 · 1h 19m · news
Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996 · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this 20VC episode, host Harry Stebbings interviews Jackie Reses, Chair & CEO of Lead Bank, exploring her journey from a gritty childhood to orchestrating legendary $50 billion deals, her outcome-driven hiring and leadership philosophies, and her strategic vision for the future of fintech and compliant banking infrastructure.
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 15.8% of the talking time here. How this is scored →
Harry as informed peer 2.4 Guest teaching 3.9 Guest disagreement 1.4 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 41:52 Rejecting micromanagement premise
Reses directly rejects the premise endorsed by Shopify CEO Tobi Lutke, stating flatly that she does not agree with micromanaging except in cases of performance management.
Hardest push from Harry ▶ 29:24 Calling BS on VC 'leaning into winners'Stebbings strongly rejects standard venture capital advice to lean into winners, calling it bullshit and arguing that strategic trimming yields better long-term fund returns.
Biggest teaching moment ▶ 1:07:02 Explaining anti-network effects in bankingReses reframes financial platform risk by introducing the concept of anti-network effects, explaining how compliance failures by one client create existential regulatory risk for all others.
Harry holds his own ▶ 45:23 Challenging crypto's central bank disintermediation premiseStebbings uses macroeconomic principles to challenge the notion that central governments would ever allow private cryptocurrencies to displace sovereign monetary control.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Childhood Memories, Family Entrepreneurship, and Defining Grit | 1 | 2 | 0 | 1 | The host opens with informal rapport-building and probing psychological questions about childhood motivations. The guest politely describes her early childhood memories, entrepreneurial family background, and definition of grit. | |
| Educational Expectations, Wharton School, and Pivotal Personal Relationships | 1 | 2 | 0 | 1 | The host asks about handling childhood expectations at age fourteen. The guest explains her family's strict educational focus on Wharton and how meeting her husband's family established her standards for excellence. | |
| Defining High Performance and Outcome-Driven Leadership | 2 | 4 | 1 | 1 | The host admits his own hiring shortcomings and asks for framework advice. The guest reframes traditional hiring, explaining how her private equity background prepared her to lead HR by identifying human strengths rather than resume bullet points. | |
| Hiring Mistakes, Work Ethic, and Building Strong Culture | 2 | 3 | 1 | 2 | The host offers a deliberate boomer-style provocation about younger workers avoiding hard work post-COVID. The guest agrees on intensity, outlining how to build high-performance cultures without entitlement through examples like Square's PPP effort. | |
| Fostering Employee Loyalty and Career Followership | 1 | 3 | 1 | 1 | The host asks what creates long-term executive followership. The guest outlines her philosophy of taking a twenty-year career perspective on people and providing direct, honest feedback. | |
| Lessons in Non-Zero-Sum Negotiation and Deal Making | 2 | 4 | 1 | 1 | The host asks for core negotiation principles. The guest explains non-zero-sum dealmaking and illustrates how she yielded on economics to protect structural governance with Lead Bank investors. | |
| Reclaiming Alibaba Equity and Strategic Risk Management | 3 | 5 | 2 | 3 | The guest details renegotiating Alibaba equity for Yahoo despite having zero legal leverage. The host pushes back against traditional VC dogma that advocates blindly leaning into winners, calling for disciplined exits. | |
| Fintech Projections: Revenue Focus Versus Expense Management | 3 | 5 | 2 | 2 | The guest delivers a detailed overview of fintech market dynamics, highlighting expense management as the next frontier. When the host confuses Goldman Sachs's Marcus with JPMorgan, the guest gently corrects him. | |
| Disrupting Incumbents, Rewarding ICs, and Opposing Micromanagement | 4 | 3 | 3 | 4 | The host cites Shopify CEO Tobi Lutke's defense of micromanagement to challenge the guest. The guest explicitly disagrees, rejecting micromanagement in favor of outcome-based leadership. | |
| Navigating Crypto Winter and Federal Reserve Regulation | 4 | 5 | 2 | 3 | The host questions how central banks could ever cede monetary control to crypto. The guest draws on her experience as San Francisco Fed Economic Advisory Council Chair to explain regulator engagement and risk assessment. | |
| Fintech Consolidation, Feature Fallacies, and the Super-App Myth | 3 | 5 | 2 | 3 | The host asks if consumer super-apps are overhyped. The guest explains cyclical bundling/unbundling dynamics and notes that super-apps like Cash App and NuBank are rare exceptions requiring rare conviction. | |
| The Vision and Unique Architecture Behind Lead Bank | 3 | 6 | 2 | 2 | The guest explains why she acquired and rebuilt Lead Bank. She introduces the concept of anti-network effects in regulated banking, educating the host on how bad actors create platform-wide regulatory risks. | |
| Quickfire Round: Books, Regrets, and Jack Dorsey's Influence | 2 | 3 | 1 | 1 | In a quickfire round, the guest shares insights on writing her small business book, living without regrets, changing her mind on psychedelic therapy, and key leadership lessons learned from Jack Dorsey. |
Statements from this episode (28)
Reses: Moved Out and Sent Herself to Boarding School at Age 14
“I ended up moving out of my house when I was 14. I sent myself to boarding school, and I got myself out of a household of chaos.”
Reses: Evaluate High Performers by Outcomes Driven, Not Work Activities
“I think there can be a bunch of different dimensions around that where people have incredible raw intelligence and they're able to actually create outcomes that matter and make a difference to a company. And so I focus on not the work they're doing, but the ou…”
Reses: Private Equity Is Fundamentally About Talent Judgment and HR
“If you really abstract what private equity is judgments about people, where you need to place them in their jobs, and what levers of growth you give them in order to help them grow a business. That is recruiting, and that is leadership, and that is HR.”
Reses: Despite a Career in Finance, I Am Terrible at Mental Math
“In reality, I'm terrible at like accounting and math on the fly. I can't do it in my head.”
Reses: Raw Intelligence and Grit Beat Domain Knowledge for Novel Products
“I would rather focus on things like raw intelligence, judgment, curiosity, grit, ability to manage ambiguity, rather than looking for things like domain knowledge or operators with prior scale experience, you know, that's another big mistake where you assume b…”
Reses: Underdog Company Alumni Make Grittier Hires Than Top-Tier Tech Employees
“Anyone who went to Yahoo was grittier than a lot of the people who worked at higher profile companies that were just minting money, and when you came to Yahoo, you had to work a little harder, and so I find places like that are incredible places to go higher, …”
Reses: Founders Must Prevent Employee Entitlements Starting With First 20 Hires
“You have to set up a culture where you don't build entitlements into the way that you operate, and I think that's really important from the first 20 people that you hire to lay out the foundations for the focus, the intensity, and the inspiration of what you'r…”
Reses: Square Mobilized Entire Workforce as 24/7 PPP Loan Reviewers During COVID
“We developed PPP, this is at Square, in a crisis. And we ended up with a core team of people working on it, and then we literally got the entire company of Square to volunteer for us to be, you know, loan reviewers twenty-four-seven during that period of time,…”
Reses: Take a 20-Year View on Employees' Careers to Build Loyalty
“I focus on the long game with people. I really care about their career, and it could be someone who is multiple levels down for me. I don't care. If I've built a relationship with someone and I want to help them, you know, I will take a 20 year view of how to …”
Reses: Self-Funding Lead Bank Provided Maximum Leverage Over Outside Investors
“We had a lot of leverage when setting up this company because I was also willing to fund it myself. And the only reason I was taking folks was because I wanted their brain.”
Reses: Regulatory Approval and Speed Took Priority Over Valuation at Lead Bank
“When we set the terms for our investing rounds, I was very comfortable letting our investors get a lot of their way on a lot of different components of the transaction because I knew I needed certain things. I needed a structure that was appropriate for a bank…”
Reses: Yahoo Earned $50 Billion Through Renegotiated Alibaba Deal
“It probably generated fifty billion dollars worth of economics to Yahoo shareholders”
Reses: Square Built Products Directly Inspired by Alipay's Capabilities
“We drew a lot of inspiration from that in what we built at Square, Because we had seen what was being built at Alipay with firsthand insight, and were able to look at that and draw inspiration from it.”
Reses: Most Investors Are Great at Buying but Terrible at Selling
“People usually are great at investing and terrible at selling, And I think I'm guilty of that myself.”
Reses: Coatue Excels at Risk Management by Avoiding Emotional Attachments
“Kotu is an investor of mine, and I look at Philippe LaFont, Thomas LaFont, and the way that Kotu manages risk, and I am mesmerized by their ability to understand market dynamics and react to it in really smart ways. They aren't enamored by the companies that t…”
Reses: Next Decade of Fintech Winners Will Focus on Expense Management
“And so, I see the next 10 years of interesting companies being developed around expenses, expense management, and then infrastructure as the second component.”
Reses: Incumbent Banks Focused Only on Cash Flow Will Fail
“If they decide that they just want to manage their business for cash flow, they will die a long-term death.”
Reses: Equating Power With Headcount Growth Is a Cancer on Innovation
“This idea that you need to, like, keep growing teams in order to become more powerful in a company is like a culture killer on invention. You could have people who are incredible, who are just incredible operators in their own, and they need to be rewarded as …”
Reses: Lead Bank Is a Net Beneficiary of Crypto Market Scrutiny
“There are some components for us as a bank that are also interesting because we understand how to assess risk in the crypto market, and we have been able to onboard those crypto companies that are super high quality companies that are getting unbanked by those…”
Reses: No Current Crypto Use Case Has Proven Market Longevity
“I don't think we're there yet on any use case, frankly. That I think will have longevity in the market, but I do think the underlying technology is super important to experiment with and to explore new ways of building financial rails”
Reses: The Federal Reserve Has Done a Great Job Learning Crypto
“And so I have seen in the last few years a willingness to dig into crypto in a way that is profoundly different than in the past, where regulators might have had a more limited interaction with companies. I think they truly understood that they needed to under…”
Reses: Wave of Fintech Market Rationalization Is Coming for Weak Startups
“And given the increase in funding that happened, I think there's a 10 X increase in funding over the last few years, you will see the rationalizing of this market with companies that just haven't achieved product market fit.”
Reses: Feature-Based Consumer Fintechs Will Disappear Over Time
“And so I do think there are many consumer fintechs where I just don't see the differentiation in the product to truly stand the time or their features. They're not companies. And they should be integrated into other products that can help build LTV. Cause I do…”
Reses: Super Apps Are a Myth Except for Outliers Like Cash App
“And so, I don't see a broad market for super apps. I think there are a few players out there who have shown that they could build multiple use cases around their product. Again, I got to go back to Square because I know it so well. Cash App is, to me, the most…”
Reses: Dorsey Locked Himself in Square's Office to Build Bitcoin Integration
“I remember in 2017, maybe, yeah, it was end of 20 16 when Jack wanted to put Bitcoin into Cash App. And he, ah, two engineers sat, ah, on the sixth floor of 14 55 market and wouldn't leave the office until they were able to build that product.”
Reses: BaaS Middleware Providers Are Suboptimal for Scaled Fintechs
“And I think those companies are fundamentally in a middle spot. They're not the final decision maker of a bank. And so if you're a scaled fintech, that's not an optimal place to be. From who you want to work with, because you can't actually control the decisio…”
Reses: Partner Banking Is an Anti-Network Effects Business Due to Regulatory Risk
“Any of our customers can harm another customer because regulators look at our customer base and can make decisions about the overall company that if we are not in compliance, they could limit how we operate, and I think you've seen that with some of the banks …”