The Twenty Minute VCWilliam Hockey: How I Founded Plaid; The Ultimate Cold Email Tip; Hiring Lessons | 20VC #955
CHAPTERS
- 0:00 – 2:07
From farm tinkerer to founding Plaid and starting Column
William Hockey shares his non-traditional path into startups, rooted in a hands-on upbringing and a love of building. He explains how programming became his outlet in college and how side projects with his co-founder led to Plaid—and eventually to the idea for Column.
- •Grew up building physical things on a farm; identity as a builder/tinkerer
- •Learned programming in college as a practical way to create
- •Started Plaid senior year with co-founder Zack
- •Plaid’s vantage point revealed systemic issues in financial infrastructure
- •Column emerged from a long-held desire to build inside the regulated perimeter
- 2:07 – 3:25
Why most fintech is built outside regulation—and why Column went inside
Harry challenges why fintech founders avoid the regulatory perimeter. William lays out why Silicon Valley’s playbook (fast iteration, low upfront capital) clashes with regulated banking, and why Column required buying an OCC-regulated bank and accepting a slower ramp.
- •Regulated businesses demand large upfront investment and time
- •Column acquired an OCC-regulated bank to operate as a real bank
- •Regulation intentionally slows change; long build before “hockey stick” growth
- •Two engineers in a garage can’t realistically build a bank from scratch
- •Silicon Valley incentives favor simpler, tech-dominant success paths
- 3:25 – 6:31
What are you running from/towards: pragmatism over “100-year” narratives
A reflective segment on motivation and temperament. William contrasts pragmatic problem-solving with the tech world’s tendency to frame work in grand future narratives, and discusses how founders should understand their own idealist vs. pragmatist leanings.
- •Work ethic and grit shaped by rural upbringing
- •Preference for tangible problems society has today vs distant futurism
- •Critique of “world-changing” language masking mundane products
- •Founders benefit from self-awareness about their natural style
- •Pragmatism as a durable operating philosophy
- 6:31 – 8:01
High performance as quiet, long-duration execution
William reframes “high performance” away from visibility and status. He argues the highest-performing builders can grind for a decade in obscurity, focused on compounding progress without needing constant external validation.
- •High performance = sustained execution without recognition
- •Early founder desires: fame, cool parties, money, validation
- •Real companies take 10+ years to realize value
- •Ability to operate ‘in the shadows’ correlates with long-term success
- •Focus and endurance beat short-term signaling
- 8:01 – 11:05
Ego, identity, and taking big swings without needing the spotlight
The conversation turns to ego and identity attachment to company outcomes. William argues everyone craves validation, but the most effective operators learn to model themselves after low-profile builders and maintain a stable identity beyond company status.
- •Everyone has vanity; the key is balancing it honestly
- •Role models: complex, boring, behind-the-scenes capital compounders
- •Stepping away from Plaid at its peak as evidence of identity separation
- •Keeping long-term friends outside founder/status circles as a grounding force
- •Identity security enables bigger, riskier swings
- 11:05 – 12:14
Money and risk: buying time for longer-horizon problems
Harry probes how wealth changes risk appetite. William explains money primarily buys time and reduces immediacy pressure, enabling work on long-duration problems—while acknowledging prior success provides psychological validation for a second swing.
- •Prior success increases willingness to attempt a second big venture
- •Wealth reduces ‘I need a job now’ urgency and fear-driven decisions
- •Capital enables longer shelf-life projects with delayed reward
- •Thoughtfulness increases when immediacy pressure is removed
- •Risk appetite is shaped by both resources and personal grounding
- 12:14 – 15:54
Leadership evolution: constrained resources, delegation, and building “to the turtles”
William contrasts Plaid’s boom-era, well-funded environment with Column’s self-funded, employee-owned model. He explains how resource constraints shape leadership, and how Column differs by rebuilding the stack from the base layer rather than abstracting legacy complexity.
- •Leadership change is gradual, but context changes behavior
- •Self-funded constraints demand sharper prioritization and pragmatism
- •More delegation required when resources and time are tightly managed
- •Many Silicon Valley winners abstract legacy complexity (Stripe/Twilio/Plaid)
- •Column aims to rebuild from the ‘bare metal’ rather than add middleware
- 15:54 – 20:50
Hiring lessons: patience, role-fit (soldiers vs generals), and resisting VC speed pressure
A deep dive on hiring philosophy and the trade-offs of speed. William emphasizes waiting for the right candidates—especially early—while also acknowledging not every role needs a 1% “A+” player and that over-scaling headcount is often unnecessary.
- •Deliberate, painful patience to hire the right people (even 12–24 months)
- •Most companies say they do this; few actually follow through
- •Not every role needs a superstar; role-fit matters (soldiers vs generals)
- •Over-hiring is common; many large orgs could achieve similar with far fewer people
- •‘Move fast’ is industry-dependent; infrastructure needs correctness over cadence
- 20:50 – 23:42
Venture and long-duration regulated bets: why “more money” doesn’t solve everything
Harry argues Column is exactly what venture should fund; William responds that, in practice, venture favors businesses where technology is the primary lever. He explains why regulated banking success depends equally on risk, regulatory strategy, and expertise—areas not simply accelerated by capital.
- •Venture prefers understandable models where engineering dominates outcomes
- •Column requires tech plus regulatory strategy and risk management excellence
- •Key constraints are time and expertise more than capital
- •Fast ARR milestones aren’t realistic in regulated infrastructure
- •Self-funding can de-risk and better align outcomes for employees
- 23:42 – 25:50
Personal capital allocation: concentrated bets and ‘investing in yourself’
William describes a highly concentrated portfolio—mostly Plaid and Column—driven by his preference for depth over breadth. He contrasts safer compounding strategies with the long-horizon potential of building, and reflects on whether CEOs are good resource allocators.
- •Not highly focused on diversified portfolio construction
- •~All wealth concentrated in his companies; small tail in funds/edges
- •Safer alternatives could yield steady returns, but building may be highest long-run IRR
- •CEOs often skew risk-on, not optimal pure financial allocators
- •Market turmoil exposes the limits of aggressive risk-on allocation
- 25:50 – 27:18
Imbuing patience into the team: experience, hiring profile, and company self-selection
Harry asks how to get ambitious employees to accept slow, correct progress. William points to team composition (older average age, fewer new grads) and values-based self-selection, arguing experience with boom-bust cycles makes long-term value creation more intuitive.
- •Older team skew (average age 30+; few/no new grads) supports patience
- •Experience teaches that ‘coming out too strong’ can be negative
- •Company positioning attracts people aligned with doing it “the right way”
- •Patience is cultural and talent-profile dependent
- •Not every strong candidate resonates with long-duration infrastructure work
- 27:18 – 35:44
What Column does and the ‘money supply chain’ problem
William explains Column’s core: a regulated bank offering APIs to move, hold, and lend money. He frames legacy banking as an intermediary-heavy “supply chain,” where developers must integrate many vendors, and Column collapses that chain by connecting closer to the Fed’s underlying rails.
- •Column is a bank providing developer/enterprise APIs for core money primitives
- •Legacy model: multiple middleware providers wrapping an old-school bank
- •Developer pain: many vendors, spaghetti code, long implementation timelines
- •Fundamental issue is lack of control at the bank/protocol level
- •Column’s thesis: collapse intermediaries and go ‘straight to the Fed’
- 35:44 – 40:22
US financial system as protocol: fix implementations, not the underlying rails
William argues the US system’s underlying protocols are powerful; the failure is how legacy banks implement them. He claims much of what crypto promises (e.g., faster/always-on transfers) can be achieved inside regulated rails by rebuilding modern implementations—without needing everything ‘on-chain.’
- •Critique: people conflate big banks’ tech with the core US financial system
- •Fed/TCH rails are stronger than commonly portrayed; ‘COBOL at the Fed’ is a misconception
- •Examples: 24/7 payments and wire cutoffs are often bank-implementation limits
- •You can replicate many crypto benefits within regulated infrastructure
- •‘On-chain’ is not necessary for most practical outcomes
- 40:22 – 44:50
Global comparisons and reform: China’s speed, US governance, and balanced regulation
The discussion compares national systems and the pace of change. William credits China’s rapid execution driven by centralized decision-making, while arguing the US needs a better regulatory balance—enough protection without pushing innovation offshore into riskier jurisdictions.
- •US strength: dollar dominance; tech implementation often lags
- •China’s advantage: faster system/regulatory change due to fewer decision-makers
- •US challenge: innovate without abandoning democratic checks
- •Regulatory extremes cause harm: too strict pushes activity offshore; too lax becomes Wild West
- •Crypto as cautionary tale: punishing ‘good actors’ can increase consumer risk
- 44:50 – 52:39
Coinbase, the next decade of fintech, and vertical brands becoming financial brands
William hopes Coinbase succeeds as a regulated innovator and uses it as a lens on regulatory incentives. Looking ahead, he predicts traditional cradle-to-grave banks fade into the background while vertical software and consumer brands embed financial services, winning through distribution and customer intimacy.
- •Coinbase tried to operate within regulation and got punished vs faster rule-breakers
- •Future fintech: financial brands shift to platforms with built-in audiences
- •Vertical software firms can offer payments/lending/treasury as commodity add-ons
- •Customer relationship and distribution beat broad, unfocused product sprawl
- •M&A may be harder; more in-house building enabled by infrastructure providers like Column
- 52:39 – 55:31
Quickfire: books, cold-email rule, strengths/weaknesses, and founding with his wife
A rapid segment covering reading recommendations, career tactics, and personal traits. William’s standout tactical advice is that cold emails (plus persistent follow-up) outperform networking; he also shares optimism, pain tolerance, social anxiety, and the trade-offs of co-leading with his spouse.
- •Book recs: ‘Merchants of Grain’ and ‘The World For Sale’ (commodities focus)
- •Cold emails + 3 follow-ups as a key career ‘unfair advantage’
- •Strengths: optimism, high pain tolerance, deep focus on boring problems
- •Weakness: strong introversion/social anxiety despite outward energy
- •Co-founding with spouse: perfectly aligned incentives but blurred work-life boundary
- 55:31 – 1:00:19
Hard lessons and closing: Visa deal blocked, boards/venture realism, and the next five years
William reflects on the failed Plaid–Visa acquisition and how government decisions shape business reality regardless of fairness. He discusses boards and venture’s tendency toward self-mythologizing, then closes with a candid view that the next five years will be hard—but he expects to still be building.
- •DOJ blocking Plaid–Visa taught that government is a decisive stakeholder
- •Motivating teams post-windfall: reality plus subsequent momentum (e.g., later financing)
- •Boards add value depending on stage and incentive alignment
- •Venture should be more honest about being capital allocation (not hero narratives)
- •Personal outlook: startups are brutal but deeply fun; progress is slower than founders expect
