50 Questions re: founder fit

an exploration on how I work…

The Y Combinator suggested 50 Questions to Explore with a Potential Co-Founder…

PART 0: HOW YOU OPERATE

1. What are your strengths and superpowers (beyond functional expertise)?

  • Superpower is the chip on my shoulder. As the son of a single mom who’d worked tirelessly her entire life to provide opportunities, I refuse to quit. I also refuse to be die in tarpit ideas so I’m not so stubborn that I’m not able to pivot (we’ll speak more on this re: our biz model)

2. What are your weaknesses? How do you try to compensate for them?

  • My wife (and Operating Chief) is my weakness. I’d normally destroy/distance myself from distractions to the long term success - however the notion that I want my wife included in this adventure turns me quickly from CEO to Personal Development/Performance Coach.

  • I’m actively looking for a technical co-founder that I can look to as a thought leader, a general, a true peer in every sense of the word. That’s the ultimate reason for bringing in a 3rd to the mix.

3. What words would your co-workers use to describe you? What would they want me to know about what it’s like to work with you?

  • This questions is difficult to answer because I currently have no peers (only subordinates). We have a distributed team (I don’t know some of our own staff), so for those that are far enough from me, they’ll think I’m “nice”. For those closer to me, they’ll mistake my frustrations as mercurial, I know deeply to celebrate wins, but I care A LOT when things go wrong.

4. How do you deal with conflict? Describe a time you dealt with it well — and a time you didn’t.

  • I’m a critical path driven individual (my experience with managing fairly large architectural projects, and before that, playing real time strategy games) - when things go wrong, blame, emotion, etc. are useless in solving the problem, I’ll unpack that when it’s peacetime.

  • When things go wrong in our company, I’m normally very quick to put on the analysis/execution cap. I’ll urge the team to push forward and come up with solutions that scale.

  • I don’t deal with conflict well when shot callers in our organization (C-suite) do not behave admirably w/ hard solutions. I’ll go off the deep end and derail an hour speaking about personal development.

5. What’s the worst interpersonal conflict you’ve dealt with? How did you handle it?

  • There was a point in our survival story when I wanted to fire my wife. It was difficult to come to terms with the notion that she might not be “good enough” for the hardest adventure of all.

  • I dealt with it by realizing that focusing on my own work and development is ultimately the solution.

6. How do you cope with stress? Depression? Are there any red flags I can help watch out for?

7. How do you arrive at your convictions? What are some key mental models you use to be creative, solve problems, or make decisions?

8. Describe your work style. What techniques do you use for personal productivity?

9. How many hours/week are you willing to work? For how long? What sounds good? What sounds like hell?Do you have different expectations for different phases of the company’s lifespan? (i.e. willing to work harder in the beginning)

PART I: ROLES

10. What would you want your role to be before we reach product/market fit? What would you want your role to be after we reach product/market fit?

  • Before PMF: I want to hunt. I want to build. I want to everything it takes for that juicy PMF

  • After PMF: I want to sell. I want to do bizdev every single day. I want to argue with you that we don’t have enough units to ship. I want you to yell at me that we’re not ready for another enterprise client.

11. How do you see your role changing as the company starts to scale? (Read the Review article on giving away your Legos.)

  • I want to sell and visioneer until we get to that plateau where we need to take on venture funding to be everywhere all at once (global/24/7/365). At that point I see my job shifting to traditional CEO leadership (maintain healthy liquidity, spin up new profit centers, identify M&A targets, etc.)

12. If your role becomes unavailable entirely (e.g. the board hires a professional CEO or an experienced executive), what would you want your new role to be?

  • Assuming we have the sex appeal to bring an incredible CEO onboard - I’d shift my gaze to be purely on market making & profit center verticalization/optimization. The vision I have for our company is that we are the digital moat around every high rise building. We’d eventually want to be the vendors for the most lucrative products/services (ala Amazon Essentials copying best sellers and displacing incumbents).

13. Areas of Responsibility (AoR) Exercise. Rank yourself in these areas (both as an individual contributor, and as a leader) on a scale of 1-10. Then rate your passion in each of the above areas on a scale of none to high. (e.g. “I’m an 8 in sales, but hate it so none”):

  • Sales

  • Marketing

  • Product Strategy

  • Design

  • Engineering

  • Operations

  • Fundraising

  • Leadership

  • Company Building

  • Recruiting

  • Legal

  • Specific Skills* Domain or technology-specific skills (e.g. Healthcare, Machine Learning, etc.)

A. Cluster AORs based on rank and discuss how they could be assigned to individuals. (E.g. John is a 10 in product, so he gets that AOR).

B. Break ties using the passion rating. (E.g. Nick is a 7 in sales with medium passion and Gloria is a 7 in Sales with high passion, so Gloria will take on sales).

C. Discuss: Do these clusters align with everyone’s expectations, skills, and desires? Do we all agree on the areas of responsibility for the CEO, CTO, COO, etc?

PART II: CORPORATE STRUCTURE AND FUNDING

14. Where should our startup be based? How do you feel about remote or distributed teams?

  • Ultimately, I think we should be where talented/ambitious/smart people are. I’ve had experience with distributed teams and there’s something electric that happens when passionate/smart people get together, get a little sauced up and say what they really feel. I think senior leadership needs to be under 1 roof (literally, I want to live in a high rise w/ all of our shot callers).

  • The nature of our business (managed marketplace) will require a distributed team (at least from a service/fulfillment perspective) so we better get comfortable with it!

15. Is there anything I should know that may affect materially affect your time or legal status as a founder? (e.g. visa, green card, criminal record)

  • Born & raised in NYC. No criminal record. Adverse to things that risk the future of our company.

16. How should founder equity be set? What’s your philosophy on the employee equity pool?

  • Eat what you kill. It truly doesn’t matter that we’ve found the limited traction we have. Making money is a byproduct of being great at something. If you’re a fucking software warrior and you’re putting out work I didn’t even know was important until I saw it, I will see the value and reward it heavily. I have ZERO qualms about people making more money than me (I think our sales staff should actually make more money than anyone in our organization).

  • Re: ESOP - important early to retain otherwise inaccessible talent. During scale, not important at all - all the important pieces should be firmly planted. Post-domination, I’d love to be like Mondragon. Not because I’m a humanist, mother Theresa, but because it’s just good goddamn business.

17. What should our approach to employee compensation be, including cash and equity?

  • Refer to #16 - early stage, it’ll be a mix of both. There isn’t a blanket policy on things like this. Certain people are rockstars, most people are just furniture. We evaluate as a committee and decide together.

18. How much money should we raise? (i.e. “zero” to “as much as we can”) In the range of “bootstrapped small business” to “go big or go home”, where do you want this startup to go?

  • I prefer to bootstrap BUT not at the expense of speed. We already have carved a wonderful lifestyle business for ourselves. Now it’s about reach.

19. What matters most in a funder? If you were doing reference checks on a VC or potential board member, what traits would you be looking for?

  • Utility and/or Guidance. Utility being a VC that’s invested into a business that is in a market we’re trying to crack (i.e. government contracting) and during the road show, we ask SPECIFICALLY for that utility and make certain it’s part of the deal.

  • From a Guidance perspective - it’ll be self evident. If we get to speak to a Perkins, Horowitz, Kholsa, etc. we STFU and take the money.

20. What does an ideal company exit look like to you? (i.e. “work on company for 1-2 years and sell for 7 figures” to “work for 10 + years, reach 9 figures in revenue, and IPO”)

  • 10+ years minimum (I’m already at 5) - be in a position of market dominance (final stages of the capitalism game ala M&A rollups). We maintain private/IPO - I don’t care, I’ll borrow against our shares to buy the warehouse. “I’m not fucking leaving!” - Ben Franklin probably

21. How do you think about the timeframe and pace of success? Are you willing to take the longer path? How long is too long?

  • This really has to do with the market potential. I may have overestimated the TAM (or the difficulty of becoming a market leader). If that’s the case, it has to do with comfort. I’m past the ramen budget phase of my life. If we’re bringing home enough to be comfortable AND fund growth (while maintaining default alive status) - we can go the slow boil route.

22. What number would you sell at? How would that change if you got extra liquidity from your existing position?

  • I’m not looking to sell. I want to be in a position to create incredible things. This is the ultimate adventure, I’m looking to stay on this ride.

23. What do we do if we find product/market fit, yet none of the founders are excited about that product?

  • I can’t even imagine a world where post PMF, things are dull. The very essence of every single business is identical. Stewardship/Sales/Marketing/SupplyChain/etc. We should be an elite team of operators that play the game like its the Olympics no matter the venue.

24. Can one co-founder fire another co-founder? Can someone else fire a founder?

  • Breach/Dereliction/Criminality = Death. If any of these are present, its not about permission, its about duty. Made (wo)men can put hits on other made guys. We’ll also put governance controls into our board policies so that it maintains that line HOWEVER, we’ll be wary of raider/enemy maneuverings.

PART III: PERSONAL MOTIVATION

25. Why do you want to start a company — in general, and in particular right now?

  • I worked at a company for a decade before jumping into the abyss. This journey is truly one of kind - it requires the best of us, the highest expression of who we are/want to be.

  • There’s a saying, “born too late to explore the earth, born too early to explore the universe.” It filled me with existential angst until I realized how rich our present is. We’re at the precipice of great technological evolution, it’s absolutely the perfect time to start.

26. What is success to you? What motivates you personally?

  • Success is the ability to flex the parts of you where you find deep meaning. I’ve found joy in this game.

27. What impact do you want to have? Is your startup objective “getting rich” or “changing the world”? Is control or success more important? (i.e. Are you willing to step aside if the company is more likely to have a financially successful outcome or is it important for the founders to stay in control of the company’s destiny?)

28. What makes you gritty?

29. Who do you admire most in your organization/family/friends and why?

  • I admire my wife deeply. She’s the most well rounded individual I’d encountered on this side of the game. When she works, she’s plugged in. When she plays, she’s radiant. When she decides it’s time for family, she has the most unyielding stamina for obligation I’d ever witnessed.

30. What are you most proud of in your work career or life to date?

31. When have you taken a chance when others did not? Or when have you been willing to take an unpopular stance?

32. What are some of the products and companies you love, and why?

33. Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)?

PART IV: COMMITMENT & FINANCES

34. Will this company be your primary activity? Do you have any other time commitments?

  • There’s nothing more important to me than assembling this spaceship to guide us through this life.

  • Our holdings company (AAO Hospitality, Inc.) has equity in several consumer projects that I have a negligible bandwidth allocated to. The occasional interaction helping guide partners specifically in their retail, brick & mortar endeavors.

35. What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?

  • I am (and have been) running this full time. Ideating the path to the next peak has taken most of my bandwidth.

36. What is your personal runway? Current burn rate? Would you invest your own money (ideally retaining higher equity in return)?

  • I have an unlimited runway for the current scale of PureSpace. Having fixed structural cashflow issues, profitability per deal, etc. I am fully committed to the evolution of PureSpace into the next phase.

37. What is the minimum monthly salary you need to survive? To be comfortable? To feel like you’ve “made it?”

  • I can survive on $0 - Stella and I haven’t taken salaries from PureSpace since it’s inception. At it’s nascency, because we couldn’t afford to take money out. Now, because we want every soldier deployed to the front.

38. What should the policy of co-founders advising/consulting with other companies be?

  • Bandwidth allocation aside (don’t give up so much of yourself that there’s nothing left), I feel we have a first market advantage that should be held tight to the vest. Conflict of interest should be an open conversation.

PART V: TEAM CULTURE

39. Complete the sentence: It would make you proud to hear people describe this company’s culture as _________________. (Values are written words, and your culture is how you actually live those written words.)

40. What’s your philosophy on how to attract and retain great people? Tactically, how would we make this happen at our company?

41. What processes or techniques would you use to get the most out of your team? For example, how would you help them become better managers or achieve their goals?

42. How much of your time do you hope to spend either working or socializing with coworkers?

43. How important is diversity & inclusion? Concretely, how would you put that into action?

PART VI: CO-FOUNDER RELATIONSHIP

44. Specifically, how are we going to prioritize and make time for our co-founder relationship as we get increasingly busy with company building?

45. How would we resolve personal conflict between ourselves? How about stalemates?

46. In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce?

47. What happens in the scenario where we aren’t growing? How would we diagnose the problem? How have each of our capabilities and approach contributed to growth failures in our pasts?

48. In every partnership, there are times when a partner might breed resentment if certain dissatisfactions don’t change over time. How would you deal with a situation like this?

49. How would you think about bringing on a third (or N+1) cofounder?

50. Wrap up question: Now we know each other’s weaknesses, passions, needs and constraints––how are we going to make each other successful? What would it take to feel truly partnered in this adventure?