The Startup Founder Test

"The best time to start your business was yesterday. The second best time is today."

I love that quote. It speaks to bias for action and taking hold of the unknown. I have always appreciated that trait in startup founders. It’s taps a renegade spirit. This is probably why I have taken the leap multiple times with my own startups. It also explains why I have on occasion adopted the accent of an 18th century pirate.

Tech startups are the riskiest of any type of business you can embark upon. You are on the forefront of technology inventing new business models that can effectively scale. Almost everything is unknown requiring numerous iterations, failures, and pivots to get right.

While startups seem like all-or-nothing, insane leaps of faith, the founders that tend to find the most success are in fact quite intentional. Best entrepreneurs I have met are not unhinged risk takers. Instead, they are calculated risk evaluators, carefully weighing the pros and cons of particular ventures.

That does not sound adventurous or pirate-like. However, it would be reckless to dive into the startup world without considering a few things. For example, if you are younger, you may not have much experience, track record, or connections to lean on. Whereas older entrepreneurs often have family and financial responsibilities to weigh before quitting their job.

Before you burn the boats, as the famous saying goes, here are 39 questions to ask yourself before you launch into your startup adventure:

1. Do you have innate curiosity for ideas? Most founders have an accentuated sense of curiosity and an obsessive nature to follow their curiosity. If you do not that level of obsession about the idea or problem, it is easy to lose interest and give up.

2. Do you have an insanely big vision? Startup founders should want to solve big problems and have massive impact in the world. Startups are super challenging, so do you want to work on something that is less than crazy ambitious?

3. Do you see yourself doing this for ten years? Most startups do not have an exit for at least 7-10 years, so you got to ask yourself if you really have the stamina and focus to work on one thing for a decade.

4. Do you know your strengths and weaknesses? Startups will test you and stretch you well beyond what you have ever experienced. You should therefore be self-aware enough to know what you are good at and where you will need more help.

5. Do you know what you value most in work? Along with knowing where you are most skillful, you should also be aware of what you like in your work environment and the values you most aspire to as you are the one that will build the startup’s culture.

6. Do you have passion for solving problems? Beyond just solving for the startup idea, you will experience lots of other roadblocks and challenges to build the business. You need to have the attitude that it does not matter, you can solve whatever comes your way.

7. Do you have a strong bias for action? No one else can do the work for you. You need to have an A-type personality that makes decisions quickly, sets the schedule, and creates momentum for the startup without someone else telling you to do so.

8. Do you possess an insane obsession to detail? You are the last word on quality control. While you want to be careful of over-indexing on perfection, you also need to beware of good enough. Customers are discerning, so pay deep attention to customer experience.

9. Do you feel OK being in a state of ambiguity? Most things are unknown when you launch a startup. That is some of the fun of startups, going through the discovery. For some though, it is incredibly stress inducing. Are you able to thrive in this environment?

10. Do you know the biggest unknowns you will face? Even though a lot may be unknown at the startup, you should have done some initial research into your market and product space. Let that give you a head start to help reduce the ambiguity.

11. Do you have personal financial runway? Startups can devastate founders financially. Many overextend themselves with credit cards or loans to extend their startups’ runway. Make sure you have a financial cushion, so you do not have to ruin your credit.

12. Do you have a professional network? While not always critical when you launch, having a network can significantly ease the burden of finding talent, investors, and customers. Do not neglect networking as you build up your startup!

13. Do you have industry knowledge? Depending on what you are building, you might need some experience in the industry that you are building a solution for, especially for fields that are highly technical or heavily regulated like spacetech or biotech.

14. Do you have industry connections? Besides experience, knowing the right people can help you navigate more efficiently and faster in the industry, whether it is warm intros to potential customers or partners, finding the right talent, or providing credibility.

15. Do you have past entrepreneurial experience? Having previous startups can help you be aware of what is ahead. Also, some investors lean on previous startup experience of the founder when evaluating startups.

16. Do you prior leadership experience? Many founders go into startups never having led teams before and end up learning (and failing) on the job. Past experience as a leader though can be beneficial as you build the team.

17. Do you have an impressive background? This means having top colleges or employers in your past or notable awards and recognition. While having such a pedigree can help open up some doors, it is not required to be successful.

18. Do you know how to sell? The ability to sell is a must for every founder. This does not mean just selling product to customers. You are selling when you pitch the startup to investors or potential employees. Learn how to sell your story!

19. Do you know how to code? This used to be absolutely required years ago when the tech was harder. With more resources and AI, it is not as critical, but having some technical knowledge, whether coding or infrastructure, will be an advantage.

20. Do you know finance and accounting? It is easy to forget in the excitement of building product, you are building a business. Having some financial knowledge can help you better manage your capital, so you do not run out of funds prematurely.

21. Do you need co-founders? You can be successful as a solo founder. Having others to build with though can help accelerate your progress and give investors more confidence in your startup’s chances.

22. Do you know any investors? If you are just starting out, you probably have few or zero connections to angel investors or VC’s. It is not hard to build those relationships over time, but having some connections at the start can jumpstart your fund raising.

23. Do you need initial seed capital? Every startup begins bootstrapped. In fact, it is better to delay fund raising till you have a product and some traction. But some situations may call for outside capital at the start like capital intensive businesses.

24. Do you have access to startup community? Even if you have a team, launching a startup is an extremely lonely journey. Having a community of other founders can be valuable for sharing ideas, finding resources, asking questions, and getting help.

25. Do you know other startup founders? Knowing others that have been on the journey or are currently building a startup can be a good resource for questions or support. Often, the only people that can truly understand your challenges are other startup founders.

26. Do you have support of family and friends? The people that always have your back are those that love and know you best. Let them know what you are going through, even if they may not understand it or discourage your startup pursuit.

27. Do you have family or loved ones to care for? If you are the main caregiver or salary earner for the family, a startup will put enormous strain on your time and resources, so make sure you fully understand the implications before launching a startup.

28. Do you need to get personal matters sorted out? Because of the pressures and time constraints of startups, clean up your personal stuff ahead of the startup so you can be in a clear mental and emotional state.

29. Do you have the resources to build an MVP? If your MVP requires writing software, you might need developers. Perhaps you need to procure product ahead of time or create physical components. Whatever is required, know what you need ahead of time.

30. Do you have experience hiring people? Hiring is incredibly hard to get right even for founders that have lots of past experience. Knowing how to find talent and build a hiring process can greatly help in getting better candidates and results from hiring.

31. Do you know the potential regulatory potholes? Even if you are not building a startup in a regulated industry like banking or healthcare, there can still be legal and compliance issues related to your startup. Research that ahead of time.

32. Do you have the ability to trust others? Many founders go the solo route because they have issues trusting others, but at some point, you will need to trust people, whether employees, customers, or investors otherwise you will impede your ability to grow.

33. Do you feel uneasy when facing conflict? People disagree all the time, that is life. As a founder, you will face plenty of conflicts. You need to be at peace with this reality, learn how to navigate difficult situations, and get what you need despite disagreements.

34. Do you have the guts to fire someone? No one likes letting go employees. As a founder, you may have to lay off staff to lower costs, dismiss poor performers, or fire toxic employees. You have to be willing to do these things without hesitation or delay.

35. Do you have a timeline for goals you want to hit? When it comes to startups, most plans quickly get thrown out the window. However, you should have some vision for the key milestones you wan to achieve at the start.

36. Do you have a quit date if you have no progress? It seems morbid to plot your demise before you begin. Having a timeline for when you need to see traction can prevent you from spinning your wheels on pursuing an idea that you cannot make work.

37. Do you accept failure? For high achievers, failure seems terrifying. However, failure is not just expected, it is necessary for success. Being OK with failure is what leads you to learning faster and getting closer to product-market fit.

38. Do you want to win? Startups are a grind. Customers churn, deals wither, employees quit, and competitors will barge into your market. You got push through the obstacles and have the competitive spirit to not quit when things get tough.

39. Do you have in depth experience with Kubernetes? Joking! You do not need to over-engineer your product early on. However, you should absolutely understand how to optimize and manage costs of building in the cloud so you can extend your runway.

As you assess yourself using the questions above, what are some potential weaknesses and strengths you have as an entrepreneur. Do you feel you have what it takes to make the leap and launch a startup today? Are there perhaps other questions that you think are worth adding?

MARK BIRCH

Given the US Thanksgiving holiday and my attending a wedding, I decided to delay this edition of the newsletter for a few days. If you are in the US though, hope you enjoyed your turkey!

The past couple of weeks have been a whirlwind. First, I traveled to Taiwan to speak on the main stage at Meet Taipei. Then I hopped over to Hong Kong to catch up with my AWS crew they left for AWS re:Invent in Las Vegas. Lastly, I landed in Brisbane for a fireside chat about community and startup ecosystems.

What was Meet Taipei like? It was absolutely packed with startups folks, entrepreneurial energy, and lots of collaborative spirit between private sector, investors, and government agencies. It was also encouraging to see a strong international presence with startups from Japan, Korea, Hong Kong, Poland, Czech Republic, and many other nations exhibiting. I shared some thoughts about the Meet Taipei conference in this LinkedIn post if you want to learn more.

While my time in Brisbane was short, I am glad I was able to connect with local startup founders and government ecosystem leaders helping to support the entrepreneurship, innovation, and the startup community in Queensland, Australia.

I had a stellar afternoon chatting about community & startups in Brisbane yesterday at The Precinct, one of the newer startup hubs in Brisbane. I also learned that the ecosystem has been rapidly growing, with Brisbane rising 13 spots to 34th on the latest list of world's top startup ecosystems!

Next stop is back to Taiwan for the weeklong Hacker House in Kaohsiung from Dec 8 to 14. I will be in Taipei through from Dec 6 – 8 and Dec 15 – 18, so happy to meet up if you are in either place over these next three weeks for the holidays!