I recently started a passion project with my friend to document the journey of successful Singapore entrepreneurs and get them to share their stories with us.
Having failed 2 businesses before, I thought it would be fun to interview entrepreneurs who’ve already been through the whole journey and learn how they did it from scratch.
Next week, we have the privilege of interviewing an entrepreneur who scaled his company from 0 to $100M/year in only 4 years, completely bootstrapped.
We have a few questions prepared, but we would love to get feedback from the r/Entrepreneur community as well so the interview can benefit as many people as possible.
Once this interview is done, we hope to transcribe it into an article that can become a valuable resource for other entrepreneurs to read too.
Looking forward to reading all of your responses!
What was the action that changed their direction after which there was no looking back? - finding a mentor, getting a big ticket client, inventing something
What are the various ways to get early adopters and how effective are those?
What do they look in someone before hiring them or making them their business partner and how important is the understanding of human nature in business
What’s the top 3 things you wish you did (or changed, or didn’t do) early on?
What would you tell yourself if you could go back X years?
- How do you build trust with your first customers?
- When bootstrapping a product business, what are the drawbacks of augment cashflows by doing consultancy, jobs on the sides and how to mitigate them?
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I’m always most interested in the non-business question: was there a toll on your personal life/relationships and, if so, was it worth it?
Survivorship bias interviewing successful/viable business owners but always interested in the answer.
How did you overcome the hardest challenge when you run this business?
How do you decide when to go all in?
“Can I ask you six more questions?”
I would ask what he would do if he had a 9-5 job and had no money saved
What drove you to £100m when you could have easily tapped out much earlier with less risk/stress for say £10m? I’m currently wrestling with this Q - I can sell my business right now for enough cash to live very comfortably for the rest of my life. However, for some reason, I want to roll my equity over and keep growing the business - even though there is a risk I could be left with nothing (technically unlikely but you get the drift).
I‘d only ask on thing:
„Is it possible for you to invest 2 M to replicate your success and have me do it? You bring the plan and the seed money, I‘ll execute. We‘ll split profits“.
What percentage of your success would you attribute to just being lucky? (E.g Born to a good family, being in the right place at the right time, having growing customers, having good stakeholders etc)
There’s already a company which does the exact same thing. And has been doing it for decades. It’s called Forbes. Might want to have a look.