Skip to main content
Invest Like the Best with Patrick O'Shaughnessy

Sam Hinkie - Find Your People - [Invest Like the Best, REPLAY]

77 min episode · 2 min read
·
Sam Hinkie

Episode

77 min

Read time

2 min

Topics

Career Growth, Productivity, Relationships

AI-Generated Summary

Key Takeaways

  • Digital Breadcrumbs Research: Hinkie researches founders by reading their old blog posts, GitHub repositories, Medium highlights, YouTube videos spanning years, and even interviews with their parents to understand thinking evolution and depth of expertise over time rather than relying on pitch meetings.
  • Interview Depth Testing: Rather than scripted questions, drill down on topics candidates care about until reaching the limit of their knowledge. This reveals how people learn and think versus what they know. The best candidates acknowledge expertise boundaries and distinguish between 70th percentile versus 95th percentile knowledge.
  • Trust Compounding Strategy: Build fewer, deeper relationships with hundreds not thousands of people over decades. Tell people things not in your own interest. Do things in others' best interest unconditionally. This creates a network that sends valuable insights daily and provides leverage when making decisions or recruiting talent.
  • Hiring Tournament Structure: Eli Witus sent Hinkie three exceptional blog posts within weeks, each forwarded by multiple people. Hinkie hired him based on public work demonstrating expertise before meeting. Run tournaments where candidates demonstrate actual work quality, not interview performance, making the best talent the top seed from day one.
  • API-First Business Philosophy: Outsource everything except your single area of edge. Companies should focus resources on one to three competitive advantages maximum while using specialized vendors for payments, communications, and infrastructure. A ten-person engineering team building payments infrastructure wastes time competing against Stripe's dedicated experts.

What It Covers

Sam Hinkie discusses his transition from NBA executive to venture capitalist, emphasizing deep research on founders through digital breadcrumbs, building trust through long-term relationships, and applying sports talent evaluation principles to startup investing.

Key Questions Answered

  • Digital Breadcrumbs Research: Hinkie researches founders by reading their old blog posts, GitHub repositories, Medium highlights, YouTube videos spanning years, and even interviews with their parents to understand thinking evolution and depth of expertise over time rather than relying on pitch meetings.
  • Interview Depth Testing: Rather than scripted questions, drill down on topics candidates care about until reaching the limit of their knowledge. This reveals how people learn and think versus what they know. The best candidates acknowledge expertise boundaries and distinguish between 70th percentile versus 95th percentile knowledge.
  • Trust Compounding Strategy: Build fewer, deeper relationships with hundreds not thousands of people over decades. Tell people things not in your own interest. Do things in others' best interest unconditionally. This creates a network that sends valuable insights daily and provides leverage when making decisions or recruiting talent.
  • Hiring Tournament Structure: Eli Witus sent Hinkie three exceptional blog posts within weeks, each forwarded by multiple people. Hinkie hired him based on public work demonstrating expertise before meeting. Run tournaments where candidates demonstrate actual work quality, not interview performance, making the best talent the top seed from day one.
  • API-First Business Philosophy: Outsource everything except your single area of edge. Companies should focus resources on one to three competitive advantages maximum while using specialized vendors for payments, communications, and infrastructure. A ten-person engineering team building payments infrastructure wastes time competing against Stripe's dedicated experts.

Notable Moment

When Hinkie called an elementary school principal about his two-year-old son's future kindergarten enrollment, detailing research on age cutoffs and Texas statutes, the principal patiently listened then asked if his son lived with educated parents in the best school district. The principal's response: your son will be fine.

Know someone who'd find this useful?

Episode Transcript

Here's an interesting question to think about. If your finance team suddenly had an extra week every month, what would you have them work on? Most CFOs don't know because their finance teams are grinding it out on lost expense reports, invoice coding, and tracking down receipts until the last possible minute. That's exactly the problem that Ramp set out to solve. Looking at the parts of finance everyone quietly hates and asking why are humans doing any of this? Turns out they don't need to. Ramp's AI handles 85% of expense reviews automatically with 99% accuracy, which means your finance team stops being the department that processes stuff and starts being the team that thinks about stuff. Here's the real shift. Companies using Ramp aren't just saving time, they're reallocating it. While competitors spend two weeks closing their books, you're already planning next quarter. While they're cleaning up spreadsheets, you're thinking about new pricing strategy, new markets, and where the next dollar of ROI comes from. That difference compounds. Go to ramp.com/invest to try Ramp and see how much leverage your team gains when the work you have to do stops getting in the way of the work that you want to do. To me, Ridgeline isn't just a software provider. It's a true partner in innovation. They're redefining what's possible in asset management technology, helping firms scale faster, operate smarter, and stay ahead of the curve. I wanna share a real world example of how they're making a difference. Let me introduce you to Brian. Brian, please introduce yourself and tell us a bit about your role. My name is Brian Strang. I'm the technical operations lead, and I work at Congress Asset Management. How would you describe your experience working with Ridgeline? Ridgeline is a technology partner, not a software vendor, and the people really care. I get sales calls all the time, and I ignore them. Ridgeline sold me very quickly. We went from 7,000,000,000 to 23,000,000,000, and the goal is 50,000,000,000. Ridgeline was the clear front runner to help us scale. In your view, what most distinguishes Ridgeline? They reimagined how this industry should work because obviously they were operating on another level. It's worth reaching out to Ridgeline to see what the unlock can be for your firm. Visit ridgelineapps.com to schedule a demo. One of the hardest parts of investing is seeing what's shifting before everyone else does. AlphaSense is helping investors do exactly that. You may already know AlphaSense as the market intelligence platform trusted by 75% of the world's top hedge funds, providing access to over 500,000,000 premium sources from company filings and broker research to news, trade journals, and over 200,000 expert transcript calls. What you might not know is that they've recently launched something game changing, AI powered channel checks. Channel checks give you a real time expert driven perspective on public companies weeks before they show in earnings or consensus revisions. AlphaSense uses an AI interviewer to run …

Get the full transcript (16,820 words) + summary by email — free

One-time email with the complete transcript and AI summary of this episode. No account needed.

One email, no spam. We’ll also show you what SignalCast does.

Browse all Invest Like the Best with Patrick O'Shaughnessy transcripts →

You just read a 3-minute summary of a 74-minute episode.

Get Invest Like the Best with Patrick O'Shaughnessy summarized like this every Monday — plus up to 2 more podcasts, free.

Pick Your Podcasts — Free

Keep Reading

More from Invest Like the Best with Patrick O'Shaughnessy

We summarize every new episode. Want them in your inbox?

Similar Episodes

Related episodes from other podcasts

Explore Related Topics

This podcast is featured in Best Investing Podcasts (2026) — ranked and reviewed with AI summaries.

You're clearly into Invest Like the Best with Patrick O'Shaughnessy.

Every Monday, we deliver AI summaries of the latest episodes from Invest Like the Best with Patrick O'Shaughnessy and 192+ other podcasts. Free for one show.

Start My Monday Digest

No credit card · Unsubscribe anytime