How does it feel to sell a business for $100m?

by | Apr 2022 | Start a Company

In this video DQventures founder, Oliver Palmer, talks about his experience growing and selling his previous business, TigerSpike, for more than $85m.

Some of the takeaways from this interview are:

  • Sometimes investors can do right by everyone by allowing founders to take money off the table. This can reduce risk for everyone, and can ensure founders don’t become defensive as their company becomes successful.
  • As a founder, it’s important to recognise what you are and aren’t good at.
  • Perhaps the most important thing you can do, as a founder, is to hire great business builders and get out of their way (hat tips to Charley Rowley, Alex Burke, Nic Newman, and Alex Hall).
  • Recognise that it takes different skills to go from 0-20 people, than to grow from 20 to 200.
  • When hiring, be conscious that culture may be your only differentiator, because as a small business you probably can’t compete for talent on price.
  • You don’t need to be a genius to start a great company. Anybody can do this.
  • Don’t think about recruitment as simply filling jobs. Instead, hire remarkable people, then give them the freedom to develop and move within your organisation.
  • Make sure that the work you are asking people to do means something to them.
  • You don’t know you can be an entrepreneur or business leader until you do it. If you’re considering starting a business, don’t procrastinate, just give it a try. These days, that doesn’t have to mean giving up your career on day one.
  • There is no one characteristic that all successful people share, but most successful people are self-aware enough to know their weaknesses. They also tend not to follow advice blindly; nor do they ignore it. In fact, successful people tend to welcome and encourage advice, while being confident enough to weigh up different opinions, then make their own decision.
  • If you do raise money, make sure you’re talking to the right investors. Approaching a $1 billion fund asking for $1m is never going to work. And you need to be confident that you can deliver a big enough return for your investors that it’ll make their effort and time worthwhile.
  • When you remove money from life, things look very different, and you realise how much time you spent previously worrying about it.
  • When you’ve exited a business and no longer need the next pay cheque, the main consideration becomes “how am I going to spend my time?”. This isn’t always an easy question to answer, and many exited founders soon get bored.
  • Don’t launch a startup to make money. Your chances of success are far higher, with much less risk, if you simply stay in your job and invest in startups as an angel, or as an LPO in a fund. But do launch a startups for a bunch of other reasons: ambition, purpose, pleasure, being your own boss, working your own hours, satisfaction, and joy.
  • For Oliver, the measure of success is how many other people he helps to achieve their own definition of success. Previously he helped a decent number of people make money, thanks to their shares in TigerSpike. Now he’s advising potential entrepreneurs through his work at DQventures.

Interview questions

Here’s a list of the questions we asked (or intended to ask!) Oliver.

  1. For background, where were you born?
  2. For people who don’t know you, what are you known for and what do you do now?
  3. What was your first job? And how did that take you to what you do now?
  4. On your entrepreneurial journey, what or who were the key influences that led you to become the person you are today?
  5. TigerSpike is probably the business that’s had the biggest impact on your life to date. Is being an exited founder what you expected it to be, and if not, what has surprised you the most?
  6. What characteristics did your business or team have, that made it as successful as it was?
  7. As a founder, what do you think are the hardest things to deal with, which maybe wannabe founders often wouldn’t consider?
  8. Throughout your entrepreneurial journey, what single thing had the biggest impact on your thinking – maybe a meeting, a person, something you saw or learned?
  9. What do you think you and your partners each did particularly well, and what were you not so good at? On the second point, how did you overcome those weaknesses?
  10. You built TigerSpike without external capital for a long time, then raised money to scale. There’s also a lot of talk at the moment about MailChimp’s $12bn sale to Intuit, despite them having raised no capital. Given what you’ve learned, what’s your view on bootstrapping versus raising capital?
  11. For anyone launching a startup, or maybe young people thinking about a career in startups, what do you think are the most important characteristics to obtain before you start (I’m thinking things like passion, ambition, network, education, confidence)?
  12. A lot of people talk about luck in startups, and it’s an easy way to dismiss someone else’s success or explain your failure. Do you think luck is essential, or do you think there’s a system for launching startup that means luck isn’t required?
  13. At DQ we talk a lot about purpose and founder-market fit, did either of those apply to your TigerSpike journey, and if not, what other factors meant purpose and founder-market fit weren’t required?
  14. Is there a piece of advice you often give but have trouble following yourself?
  15. As an exited founder, and aside from your work at DQ, what is it that you want to learn or achieve next?

Title image

Image credit: Pixabay. (No, this isn’t Ol’s house and boat!)

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