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What do you Hate?
A powerful question for understanding founder motivation
Good Questions
The question mark is one of the most powerful symbols in the English language.
Questions have the power to shape reality. They direct and demand answers, and lay the foundation for the time and attention required to address them. Someone once said, “A good question is worth more than a thousand answers.” I believe a bad question is not worth answering at all.
After interviewing hundreds of entrepreneurs about their businesses and asking LOTS of questions, I’ve come up with a few favorites.
Here’s one we’ll talk about today: “What do you hate?”
Why do I love this question so much?
The Observer Express
Don’t have time to read the entire post right now? No worries, here are the main points:
Hatred is just as powerful a motivator as love.
The context for a question is crazy important. The question “What do you hate?” is best applied in a setting where there is appropriate time and space for a richer discussion.
If an entrepreneur doesn’t hate something about the problem they’re solving, it’s a yellow flag.
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Fire
Because hatred is, arguably, just as powerful a motivator as love.
It’s commonly said in startup circles that founders should “fall in love with the problem, not the solution.” Uri Levine, co-founder of Waze (a unicorn that sold to Google in 2013 for $1.1B) even wrote a popular book with this very title.
While I couldn’t agree more with this idea, I think the flip side is what fuels a founder’s fire. Call it the yin and yang of motivation.
Some personal examples:
Family: Because I love my family, I hate the idea of anything that would bring them harm and actively work to provide protection and care.
Life: Because I love life and believe it's a gift, I hate the despair that leads to suicide. This drives me to support mental health initiatives that help people find hope and purpose.
Freedom: Because I love freedom and see immeasurable value in every person, I hate oppression and injustice. This compels me to stand up for human rights and advocate for fair treatment.
Innovation & Growth: Because I love innovation & growth, I hate inefficiency and stagnation. This pushes me to seek out and implement new ideas and technologies that drive progress and solve problems.
The Setting Matters
The context for a question is crazy important.
If I’m on a 15-minute screening call with a founder, that shapes the questions I choose to ask. After all, you can only go so deep in such a short time. In contrast, if we’re sitting down over dinner together, the questions I pose can have much more nuance and depth.
Today’s question, “What do you hate?” is best applied in a “dinner” setting, where there is appropriate time and space for a richer discussion. Ideally, I’ll ask this as a follow-up question after getting a grip on the problem they’re solving (more on that in this post), and frame it up as “What do you hate about this problem?” or “Why do you hate this problem?”
Implications
If the person doesn’t “hate” something about the problem they’re solving, I’m concerned and treat this as a yellow flag. Entrepreneurship is a tough journey, and there’s a certain “grit” that I believe can only be obtained when someone’s got a chip on their shoulder or a motivation beyond simply making money.
Final Thoughts
I’ve recently been interviewing active angel investors about the top 3 things that contribute to an investment decision. In nearly every response, the founder/founding team is at or near the top of the list.
The question “What do you hate?” is one of the most useful follow-up questions for understanding a founder’s motivation. Effective use of these 4 little words will help you conclude whether or not YOU believe this person has what it takes to build and exit a business. I hope it’s useful to you in your conversations & investment decision-making process.
What Do You Think?
What questions do you use to assess a founder’s motivation?
Weekly Observations: 3 Lessons Learned
Picking up the phone is sales magic.📞Email is a great tool. But let me tell you, it’s CROWDED. People still pick up their phones, and a few intentional phone calls this week have proven exceptionally valuable.
Make time to think.🧠This week I spent some time intentionally reflecting on the state of our business. It’s been several weeks since I’ve been able to carve out space to do this, and I’ve been reminded how important this is as CEO - if I’m not doing it, who will?
Just show up.📅Due to a variety of factors, I found myself feeling pretty discouraged several days this week. But the saying “just show up” stuck with me, and I’ve been reminded of the importance of consistency no matter the circumstances.
Weekly Links: 3 Things I Found Interesting
Thanks for reading, have a great week.
-Andrew
If you enjoyed this post, please share it with a friend, colleague, or anyone else who may benefit.
P.S. - I recently finished creating The Angel Network Toolkit: 90 Resources for Cultivating a Thriving Community of Pre-Series B Investors, and I’m sharing it with anyone who refers a friend.
How did I do this week?
About Me
I cultivate flourishing.
I'm also the CEO of PitchFact, where our mission is to cultivate flourishing specifically through efficient and collaborative early-stage diligence. I'm a proud husband, grateful father, and honest friend. My love languages include brisket, bourbon, and espresso.