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On the Startup Team

TVLP ( is an organization that helps startup companies outside Silicon Valley understand Silicon Valley a little better. The entrepreneurs come to the Valley for a "bootcamp" style experience, to learn from those of us who have been in the trenches here.

As part of that, I gave this talk on how to build teams for (software) startups.

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On the Startup Team

  1. 1. On the Startup Team William Grosso, for TVLP
  2. 2. About Me • Serial Entrepreneur • Teams have ranged from 4 people to 140 people • Came up through the “product side” • Have worked at ~10 startups • On advisory boards for roughly a dozen more • Software guy, AI guy, Hard- problems guy
  3. 3. Outline • Preliminaries • About Startups • Team Size • What I Hire For • Tuning the Team • Case Studies
  4. 4. Startups (Mostly) Solve New(ish) Problems by Applying New Technologies and Techniques If it was well understood, it’d be on the shelves at Walmart already
  5. 5. Changing Fast and Slow Changing • The world has varying rates of change • Startups are not only solving new problems, they live in the “fast changing” part of the world • Core assumptions need to be checked constantly • There’s a lot of change in companies “right next to” yours
  6. 6. People Talk a Lot About “Going Heads Down” Going Heads Down Invariably Leads to a Pivot
  7. 7. The Right Metaphor is a Kayak on the Ocean This person does not go heads down
  8. 8. (Odd) Somewhat Glamorous • There is a cult of the startup • It is mostly misguided • Startups are a LOT of work against very hard odds • And large-scale success is mostly luck • You put yourself in position to succeed • But … you’re a tiny little boat on a very big ocean (and there are waves)
  9. 9. The Ecosystem is Full of People Who Don’t Care if You Succeed • “Service Providers” provide services to everyone • Investors are (biased) sources of funds • Lots and lots of somewhat deceptive practices and norms • Your fellow startups are all lying, constantly • “Fake it until you make it” is really “Lie to Your Customers and Investors” • Your team will be the only people who really care if you succeed or fail • Lots of people “root” for you, in the same way they root for sports teams • I love the Warriors, but I wouldn’t help rebuild the stadium if it burnt down At a guess, it has 12 users. None active.
  10. 10. Daily Psychology Curve
  11. 11. There Are (Many) “Oh Shit” Moments There are no atheists in foxholes, but there are many assholes
  12. 12. In Many Many (Many) Ways, the Best Book About Startup Management Distributed decision making at most levels Centralized, clearly articulated, high level strategy Trust and autonomy “Opposition” that is more centralized and has vastly greater resources The only management strategy that works consistently is to trust your team and delegate
  13. 13. Outline • Preliminaries • About Startups • Team Size • What I Hire For • Tuning the Team • Case Studies
  14. 14. Really? That’s the first question? You’ve got an unbuilt solution to a problem you only partially understand, in a radically shifting environment. How many people do you need to solve it?
  15. 15. The Importance of Exemplars • Find a persuasive analogy • Same TAM • Similar industry structure and forces • Talk to those companies (at least one) • Talk to them • Where were the pain points? • Pattern match against organizations solving an analogous problem • Stick to that org chart • Stick to that sizing
  16. 16. 37 Signals. Often wrong but sometimes right. Limitations Are Crucial
  17. 17. It’s very easy to overhire • It’s very easy to notice a problem, decide you need a resource, and then hire • You will run out of money • And you will never ship your product • The constraints are a part of figuring out what problem you CAN solve, and whether it has an associated business value
  18. 18. It’s Also Very Easy To Ignore Vital Skills • The “Technical Founder” who thinks she can “pick up” business skills. • Common, and huge, mistake • The “Business Founder” who thinks he can manage an outsourced dev team • The “Technical Founder” or “Business Founder” who thinks she can handle product management (without ever having done so before) • “Single Founder + Worker Bees” consistently fails
  19. 19. Outline • Preliminaries • About Startups • Team Size • What I Hire For • Tuning the Team • Case Studies
  20. 20. First-Pass: Key Characteristics • Culture Fit • Team orientation • Resiliency • Optimism • Intelligence • Curiousity • Process orientation • Has succeeded before • Village Idiots • Good Memory • Prior Passion • Actual Skills
  21. 21. Village Idiots
  22. 22. Second Pass • Willingness (and ability) to trust and delegate • Willingness (and ability) to make decisions • Willingness (and ability) to offer opinions • Willingness (and ability) to do grunt work • Willingness (and ability) to shut up once decisions have been made • Willingness (and ability) to “own” tasks
  23. 23. Not on the List • Advanced SQL-92 Skillz (buy your people books) • A College Degree • Roughly 25% of my current company doesn’t have a college degree • The ones that have degrees often don’t have them in computer science • Ability to keep a secret • Willingness (and ability) to pull frequent “all nighters” • Willingness (and ability) to subordinate entire life to startup
  24. 24. Red Flags • Can’t recall an instance where they’ve fucked up • Unable to explain current product in business terms • Answers questions in terms of minutia • Is proud of that time (or times) when she has been a super-hero and, through amazing effort and skill, saved the day • Defensiveness • Pride in specialization • Can’t recall the plan that led to the triumph • Unwillingness to hold people accountable
  25. 25. Outline • Preliminaries • About Startups • Team Size • What I Hire For • Tuning the Team • Case Studies
  26. 26. Always Tell the Story • As a leader, your responsibility is to *constantly* tell the story • You will be bored (you hear the story every time you tell it; the person you’re telling it to does not) • Always summarize what you’ve heard • Always create, and then check on, checkpoints • Always assert short-term milestones, and explain how they link to longer- term goals • If you don’t do this, it really doesn’t matter how good your team is
  27. 27. Always Articulate Goals and Standards • Related to the first one • “Standards” – this is how we do things • It’s very bad to not meet goals, and to not realize you’re going to miss them • It’s bad not to meet goals • It’s not good to meet goals through superhuman efforts (in spite of bad planning)
  28. 28. Always Delegate • As a leader, you … • Plan • Strategize • Schmooze • Make sure that everyone understands the vision • Make sure that everyone has short term milestones that they understand and are tracking to • Make sure the company is funded • You do not • Write the company blog • SSH into production servers to resolve customer-facing issues
  29. 29. Don’t Forgive • Previous slides: • You assert milestones • You assert goals • People sign up to them • If they don’t make them? • You have to hold them accountable • Single hardest thing in a startup • And very nuanced • But you have to do it
  30. 30. Have you heard about the successful startup that retained 85% of its people on a Y-o-Y basis? Me neither.
  31. 31. Outline • Preliminaries • About Startups • Team Size • What I Hire For • Tuning the Team • Case Studies