What 200 VC20 podcast episodes reinforced about great hiring
Great teams aren’t accidents. They’re built. Inside the messy, pattern-breaking hiring playbooks that actually work early on.
You don’t need another LinkedIn thread about “hiring A players.”
You need hard-won, non-obvious advice from the founders who actually built category-defining teams. Not in hindsight, but while they were still battling messy markets, budget limits, and existential doubt.
Over the last few months, I listened to 200 episodes of The Twenty Minute VC, one of the most founder-dense podcasts in tech. I pulled every mention of hiring lessons, mistakes, and philosophies from some of the world's most successful entrepreneurs: Jason Wilk, Ernest Garcia, Brian Halligan, Elias Torres, Tooey Courtemanche, and dozens more.
Here’s what kept coming up again, and again, and again once you cut through the anecdotes and looked at the patterns.
Hire for trajectory, not trophies
When you’re building a team from scratch, it’s natural to over-index on experience. After all, when you’re exhausted and scaling faster than you can plan, a résumé that says “Google” or “Stripe” looks like a shortcut to competence.
But founder after founder warned against it:
Jason Wilk (Dave): “Question every hire. Default to fewer, stronger generalists.”
Rujul Zaparde (Zip): “I’d rather invest in raw talent than in 10 years of ‘safe’ experience.”
Tooey Courtemanche (Procore): “Skills can be taught. Values cannot.”
The best founders didn’t optimize for pedigree. They optimized their hiring process around slope: the ability and desire to learn faster than the problems outpace you.
“I’d rather invest in raw talent than in 10 years of ‘safe’ experience.” - Rujul Zaparde, CEO, Zip
If you're forced to choose between a solid résumé and a steep growth trajectory, pick slope every time.
I saw this play out firsthand at SimpleTexting. As the company scaled from a team of about 30 to more than 100, people like Jennifer Hays and Lisa Wiley—who had both started in individual contributor roles—grew into Director positions in Marketing and Customer Success, respectively.
Neither had the conventional "perfect resume for the role," but both had exceptional slope. Their ability to outlearn and outrun challenges not only fueled their own rapid promotions, but helped shape the company’s next stage of growth.
You need operators before you need specialists
It’s tempting to imagine you can hire your way out of chaos with experts. If you just bring in a VP of Sales or a Head of Growth, surely they’ll impose order. Right?
Wrong.
Ernest Garcia (Carvana): “Pick operators over strategists every time.”
Brian Halligan (HubSpot): “Prioritize ‘recent relevance’ and not past titles.”
Anton Osika (Lovable): “Junior talent with oversized potential often out-executes veterans.”
Specialists are force-multipliers only once the system exists. Early on, there’s no system to optimize so you need people who build, ship, and fix, not people who theorize.
Your hiring process needs product-like iteration
Here's a brutal but liberating truth:
Your first version of a hiring process will be wrong.
Elias Torres (Drift): “If it’s wrong after a week, fix it.”
Adarsh Hiremath (Mercor): “Recruiting is the single highest-leverage function at early stage.”
Founders who scaled quickly didn’t perfect their interview rubrics in advance. They launched fast, tested hypotheses, tightened the feedback loops, and fixed obvious mistakes within a week and not a quarter.
At SimpleTexting, we lived this. We started with almost no formal process, then adopted the WHO interview framework, adding or removing steps depending on the role’s level of responsibility.
Although we flexed the structure as needed, we stuck to a familiar core — a fast, iterative approach that helped spot mistakes early. I led much of this, personally interviewed almost every hire until the team passed 80–100 people, ensuring we learned and adjusted quickly at every stage.
If a new hire is obviously a poor fit by week 2, cut bait. If interviews keep missing red flags, redesign the questions. If your top candidates keep dropping off, rework the experience.
Hiring is not a set-it-and-forget-it system. It’s an agile build.
What a great early-stage hire actually looks like
After listening to 200 episodes, the ideal profile emerged with almost eerie consistency.
Great early hires are:
High-agency: They spot gaps without being told
Values-aligned: They care about the mission the way you do
Steep slope: They’re learning 2–3× faster than peers
Recent relevance: They’ve solved the kind of problems you’re solving right now, not five years ago
Ambiguous operators: They’re energized by messy, blurry, ambiguous work
Notice what’s missing: MBAs, years of experience, fancy titles.
The founders who got it right at Series A were willing to trade polish for potential, loyalty for learning, and structure for scrappiness.
How to put this to work tomorrow
If you’re hiring today, whether it’s your 5th employee or your 50th, here’s the 80/20 move set:
Role design: Write roles around outcomes and adaptability, not tenure or pedigree. Adjust quickly if early interviews show you're attracting the wrong profiles.
Sourcing: Target "scrappy builders" — people who have built something, whether a side project, an ecomm site, or a SaaS tool — with evidence of high agency, not big brand logos.
Screening: Prioritize slope (rate of learning) over resume polish.
Interviewing: Use real-world challenges instead of hypothetical Q&A.
Decision-making: Weigh recent, relevant wins 3× more than distant brand names.
Onboarding: Set a 30-day KPI challenge to test adaptability and bias-to-action.
Final thought
Founders who hire slowly, thoughtfully, and slope-first win.
Founders who hire résumé-first, scale-too-fast, and ignore early red flags usually pay twice: once in salary, and again in team damage.
If you’re serious about building a generational company, get serious about building a generational hiring machine…before you’re “ready.” That’s the real advice nobody shouts loud enough.