Tuesday, August 9, 2022

Here’s What These 20 Millionaires Wish They Knew When They Were 20

Deathbed wishes can leave an indelible mark on a man, but they are rarely fit for practical guidance. At the sunset of their lives, people are usually concerned with the existential side of life. Have I been a good father? Did I fulfil my potential? What if I said ‘yes’ that one time?

These grand, eternal questions are by no means irrelevant. But, at 25, I concern myself with more earthly affairs. Am I in the right career, or am I just wasting my time? Do I keep my job, or is now the time to try something riskier? Such questions are especially pressing for women, who have to get their careers and family in order before 30.

Nathan Latka is a SaaS founder who spends most of his time nowadays interviewing tech millionaires. He ends each interview with a seemingly innocent question: “what do you wish your 20 year old self knew?”

Alone, each of their answers seems just as innocent as the question. But as I was sifting though more and more of these interviews, a powerful message started shaping up. I’m inviting you to see what I saw.

1. Eugene Levin, 32 | SEMRush, $102M Annual Revenue

Stop wasting time on stupid things.”

What it means for me:

Stop rewatching movies you’ve seen 7 times already — watch that controversial documentary instead; stop spending so much time with people who are not helping you build a future you want — seek out new, uncomfortable relationships instead; stop lying to yourself about what you want — rip off the bandaid of brutal honesty with yourself once and for all.

2. Erik Matlick, 49 | Bombora, $31M Annual Revenue

I don’t know as much as I thought I knew.”

What it means for me:

Read things you’d never normally read; try to understand the most ridiculous points of view; listen more, talk less; embrace the idea you’re just a work-in-progress until you die.

3. Dhruvil Sanghvi, 30 | Loginext Solutions, $18M Annual Revenue

Start as early as possible.”

What it means for me:

Don’t wait until you have more money; don’t wait until you have more experience; don’t wait until you “know what you’re doing;” don’t wait for that magical opportunity; just start. Fortune favors the ones who take action.

4. John Kim, 39 | SendBird, $22M Annual Revenue

“Things will work out, don’t give up. Just keep on focusing and life will be kind of okay.

What it means for me:

Don’t seek a fairytale endgame, for it doesn’t exist; don’t expect to build anything substantial in a day; lower your expectations and keep moving towards your dream one day at a time; don’t forget to enjoy the process, because that’s all there is.

5. Andy MacMillan, 42 | UserTesting, $84M Annual Revenue

“Focus as much on relationships as on gathering knowledge. At this point in my life, I’ve realized it’s all about the people.”

What it means for me:

Don’t expect books, movies, articles, videos or lectures to be sufficient in your dream of building a business; be a good friend, be a mentor, be a mentee, be a worthy partner, just be and let others be with you. In the end, it’s not at all about what you know — it’s about who is with you.

6. David Friend, 72 | Wasabi, $18M Annual Revenue

“To relax and not take things too seriously. I was a little fanatic.”

What it means for me:

Don’t stress over the fact you’ve only done half of your daily work quota today; don’t compare yourself to Alexander the Great; don’t set arbitrary deadlines to build your dreams or relationships. Things take more time than it seems, and that’s okay. You have time. We don’t die before we’re 40 anymore.

7. Clay McDaniel, 46 | Ripl, $10M Annual Revenue

“It’s okay to take significant career risk early. Anything you do before you’re 30 or 35 is all about learning.”

What it means for me:

Write that controversial article; quit that day job; make that cold call; send that email to Bill Gates; ask for that promotion. You won’t punish yourself for failing, but you’ll eat yourself alive for not trying. See everything as a practice run for your next big thing.

8. Jason Hsiao, 43 | Animoto, $31M Annual Revenue

“The biggest bullshit strategy advice we’ve been given and a lot of people taught us is “just try a lot of things and see what sticks.” And I just realized, man, especially for any kind of early stage startup, time and resources are limited, and you don’t have time to just try everything — that’s what a strategy is for. Be smarter about making choices and having strong rationale for those choices.”

What it means for me:

Focus. I know you want to do everything, right now. The shotgun approach doesn’t work. Choose a field, and push it to the limit until either you succeed, or until you’re proven wrong — that’s how Bezos does it. Put your back and soul into whatever you choose. Pick a problem worth solving, commit and don’t look back.

9. Nazzareno Gorni, 46 | MailUp Group, $59M Annual Revenue

“There are a lot of sources where you can learn, like podcasts. If I could have had access to this kind of knowledge 20 years ago, I think I would’ve done better.”

What it means for me:

Find competitive advantage in the vast resources available online; study psychology, business, relationships, life; everyone has access to the same information, but only few will truly investigate and internalize it.

10. James Marks, 41 | Whiplash, $9.6M Annual Revenue

“Number one, it’s going to be okay. I was so scared. I didn’t realize it at the time, but I was so scared and so… I lacked confidence in just about everything. […] I can just ask for things now.”

What it means for me:

You are enough; don’t be afraid to simply ask for stuff; people are much more friendly than you think; the hurdles are all in your head.

11. Craig Walker, 54 | DialPad, $60M Annual Revenue

“I’m running a tech company, and I was a social studies major and I went to law school. I don’t know if it’s a blessing or a curse, it would’ve probably been better to understand tech a little bit more. […] I think I would’ve been like a Computer Science major.”

What it means for me:

Think twice before choosing an academic field; don’t expect it to make or break your career.

12. Ryan Urban, 40 | BounceX, $96M Annual Revenue

“I really regret not dropping out of high school. I went to college, got a master’s degree, it was a big mistake. Some people are just made to work, I really should’ve been working at, like, 6. So I would tell my 14 year old self to drop out of high school immediately and go work for DoubleClick. I would’ve worked for DoubleClick and would’ve got a 10-year head start.”

What it means for me:

If you feel strongly that school is not for you, don’t wait and just quit; you’re losing precious time. It’s infinitely better to be wrong quickly than to be wrong slowly.

13. Niko Moraitakis, 43 | Workable, $30M Annual Revenue

“I wish I knew how easy it is to create a company and build whatever product you like and, you know, make a career of.”

What it means for me:

There are no unbeatable quests in life — and once you beat it, you will realize how much you inflated all the difficulties; take small, consistent steps; look back and laugh at how obnoxious were all the barriers you built within your mind.

14. Carson Conant, 44 | MediaFly, $19M Annual Revenue

Invest earlier in sales and marketing. You know, I’m a ‘product CEO,’ I love the product, and programmer by background, I would’ve invested earlier in marketing and sales.”

What it means for me:

When thinking about a business, don’t rely on the product; there are literally billions of products out there nobody uses and nobody knows about; a business model without a robust sales and marketing process is not a business model — it’s a creative whim.

15. Sid Sijbrandij, 40 | Gitlab, $120M Annual Revenue

It’s all gonna be okay.”

What it means for me:

Take a chill pill; people who got where you want to be were once just as anxious as you are now.

16. Vivek Bhaskaran, 43 | QuestionPro, $19M Annual Revenue

Hustle harder. Simple.”

What it means for me:

Do an extra pull up; write an extra sentence; read an extra page; it all compounds in the end, and the only thing you’ll punish yourself for is not putting in all the effort you could.

17. Prayag Narula, 35 | LeadGenius, $11M Annual Revenue

“You can always ask and aspire for more than you think you can.”

What it means for me:

Don’t limit yourself to earthly affairs; delete the word “realistic” from your dictionary; dream big, and go all in.

18. Mikita Mikado, 33 | PandaDoc, $18M Annual Revenue

“Life is amazing beyond 30s and it will probably be amazing beyond 40s, 50s, 60s, and so on and so forth. Every year is just a beginning, so take your time. Don’t try to run too fast without being present.”

What it means for me:

Don’t think your life is over by the time you’re 30; people smarter than you have realized that life is just as good after your 30th birthday; be present — the journey is all there is.

19. Olin Hyde, 54 | LeadCrunch, $20M Annual Revenue

“Take bigger risks, earlier. I started my first company when I was 25, and there was absolutely no reason why I should’ve finished college. I could’ve started my first business then and I think that the 20 year old me was too focused on becoming “prepared” for business.”

What it means for me:

If you feel strongly you want to try something, don’t wait; the journey of an entrepreneur is to find 99 ways to fail before you find the one thing that actually works. The sooner you start, the sooner you fail, the sooner you win.

20. Chris Savage, 36 | Wistia, $39M Annual Revenue

“My 20 year old self wanted to reinvent absolutely everything. Like, every single thing. It’s not customer support, it’s customer happiness. If it’s been done, I’d think it was stupid. Chris, you were wrong, because a bunch of things are just the same in any business, you should have been more open to that. It would’ve not caused you as much pain.”

Kill your ego. To succeed in business, you don’t need to invent anything. Just ask people what they want, and then do the best you can to fulfil that desire.

My 3 Takeaways From This

  1. If you’re delaying starting your own thing, don’t. No founder ever has said that they would’ve wished to gather more experience or make a few more connections or save a few more dollars before starting their company. All of them know that entrepreneurship is by and large a game of failure — and the faster you can fail, the sooner you’ll come across the thing that actually works.
  2. If you think your life will end in 5 years, don’t. At 25, I literally have nightmares of being 30. It seems to me that past that point, I will become a shade of my former self, slowly slipping into mere existence. Many founders remember feeling similarly, and their advice to their younger selves is this: take a chill pill. Life goes on, and it’s just as good as it was before.
  3. Stop thinking you’re the shit! If there’s one commonality across all founder interviews, it’s that none of them think their 20-year-old self was smart. All of them have serious criticisms and advice for their past self. If you’re unaware of your inflated ego, well, that’s just unfortunate. But if you’re aware of it and you don’t work on it — well, that’s irresponsible.

Thanks for reading.

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