As an early-stage startup investor, I look for self-aware, determined, capable, passionate CEOs who are entrepreneurial by nature and have a track record of making the seemingly impossible possible.
I like to use the first meeting to ask some fairly unconventional qualitative questions to better understand whether a startup CEO meets these criteria.
Here are 18 of my favorites:
1) Can you give your best example of something seemingly impossible that you made possible?
2) Can you give an example of a time that you thought you were up for a challenge, but had to give up?
3) What did you learn from that experience?
4) What is the most interesting thing you’ve learned about yourself from this startup experience?
5) What is the most interesting thing you’ve learned about yourself from working with your co-founder(s)?
6) If you could start your business all over again, what is one thing you would do differently?
7) If a million dollars showed up on your doorstep, and you could choose to invest it in one thing to improve your business, what would that one thing be?
8) If you were an investor considering an investment in your company, what is the biggest hesitation you'd have to overcome?
9) In the unlikely event that your company fails, what will be the most likely reason?
10) What is a piece of advice that a mentor or an authority figure gave you that you are most thankful that you ignored?
11) If you were your own mentor, what's the most important advice you'd give yourself?
12) If you could change one thing about yourself to make you a better CEO, what would that be?
13) If you weren’t doing this, what would you be doing?
14) Knowing what you know about our fund, if you could choose only one person or thing from our network or program to access, what would that be?
15) What questions should I be asking?
16) What questions do you have for me?
17) How do you think this meeting went?
18) What is one thing our fund could have done to have improved your experience with us to date?
In this latest Fund81 podcast episode, I share my 2020 plans for the Fund81 forum and podcast, and a few reflections from my short bout of holiday depression.
I’ve now read over a thousand startup investor updates. The most effective updates — the ones that immediately grab my attention and heighten my interest — have similar characteristics. My advice is below, along with a comprehensive template for startup investor updates.
At MergeLane, we’ve been thinking about how changing market conditions may affect our fund in the future. I know many of our listeners are asking themselves that question as well. Our guest, Liza Benson, thrived as a VC through both the dot-com crash in 2000 and the 2008 financial crisis.
Beezer Clarkson invests in early-stage venture funds at Sapphire Partners (the division within Sapphire Ventures that invests in venture funds). In this episode, Beezer shares her perspective on venture capital trends, VC firm differentiation, and nonobvious mistakes for VC fund managers to avoid.
As an entrepreneur and startup investor, I have had many moments of feeling like I am pushing water uphill with a rake. Sometimes, I have kept pushing and have succeeded out of sheer grit. Sometimes, it was time to admit defeat. Two years ago, I had one of those moments.
Elizabeth Yin, co-founder and general partner at the Hustle Fund, shared her thoughts on how to assess a startup’s ability to “hustle”. Her thoughts are applicable to venture capitalists, startups and anyone who wants to work with hustlers.
Nearly every email I receive starts with “Sorry for the delay.” Our always-on culture has set an unwritten expectation that an email should be responded to within 24 hours. To prevent the perpetuation of this cultural expectation, I would like to make my thoughts clear.
We asked our Fund81 forum for venture capitalists to nominate portfolio companies to participate in a startup showcase. We received over 50 nominations. Four of those startups are featured in this episode.
Jocelyn Goldfein from Zetta Venture Partners joined the Fund81 podcast to share her approach to investing in artificial intelligence (AI). With the cost of creating software continuing to decline, Zetta believes the companies of the future will need to build more than just great software to thrive.
I love being active, but I also have high professional aspirations. I’ve spent the last 16 years trying to find a productive balance between the two. In this episode, Nicole DeBoom, pro triathlete turned CEO of Skirt Sports, and I share our thoughts on how to fit fitness into a startup schedule.