Thread by @dunkhippo33

I have been a tech entrepreneur since I was in HS (20+ years). Some learnings:

1) There is a LOT of luck.

Definitely lots of hard work and skill required - no doubt. But, let's not downplay luck. Luck in everything. In privilege. In opportunity. In finding PM fit. In health.

2) A friend who has been a successful founder echoed this. His first company was highly successful.

He has been trying all kinds of startup ideas since then and nothing has really clicked.

He's smart. Hardworking. Has money. Great network. But you can force PM fit.

3) It shows up in the numbers as well.

Depending on the study you read, successful serial entrepreneurs have a slight edge over first time founders. But not by much.

4) For tech companies where the biggest risk is getting to PM fit, I'm a firm believer that experience can help you take better guesses at where there may be opportunities. It can also help you test and iterate faster. But there's still a LOT of luck in finding PM fit.

5) As such, I also think entrepreneurs shouldn't think of starting their company as 1 and done.

Being an entrepreneur is a career. Statistically speaking, you need many at bats to make it.

In your life, you probably have 5-10 at-bats if you shut down "bad ideas" quickly.

6) Thinking about "at-bats" in this way is akin to how VCs think about their portfolio construction.

A concentrated VC may have 10-20 bats in a given fund.

An entrepreneur's portfolio construction is across his/her lifetime.

7) When you think about it in this way, your mindset changes. Obviously you want THIS company to work out well. And you will do your best to make that happen.

But thinking with a "portfolio construction framework" takes some pressure off.

8) It also changes how you do business. I have been trying to work with @shiyankoh for many years now.

I asked her to join me for a startup I started in college! And then with @launchbit. Neither of those worked out. But she joined us for @HustleFundVC.

Never stop recruiting.

9) I have a list in my mind of ppl I want to work with. Most of those ppl are working on other things now. And that's fine. We don't have budget to bring them onboard. But someday, I'm sure I'll work with them.

Life is a longterm game - it's not just about a particular co.

10) In a similar way, many investors have turned me down over the years. Perhaps for my whole series of meandering websites in 2009 onwards. Or for @launchbit.

But we have brought in some of those ppl into @HustleFundVC either Fund 1 or 2.

Rejections are not forever.

11) Rejections are also NOT personal. I suppose sometimes they are. But most of the time there are circumstances you are not aware of that is happening with a wouldbe investor you are pitching.

Maybe they don't have money. Maybe you are out of thesis. Maybe they are too busy.

12) This is why I keep on pitching ppl who have rejected me before. As long as I am addressing their concerns / feedback from before, it's fair game.

I'm sure I will get my eye dr to be an investor someday.

13) And you should too! There have been many times where I have turned down founders and then they went and built something else, and I funded them.

14) Switching gears - your "at-bats" get better over time if you are constantly learning and being self-reflective and truly honest w/ yourself.

My first startup when I was fulltime in my 20s was basically a series of web projects that went nowhere.

15) I had a co-browsing site. And a bunch of affiliate sites across many categories incl wedding supplies / dresses and nutritional supplements.

All of them were terrible businesses. Why? Because I didn't think deeply about cust acq.

16) This adage is so true:

1st time founders focus on product
2nd time founders focus on distribution

I hope to help many 1st time founders avoid the cust acq mistakes I made as a 1st time founder.

17) Specific learnings incl:

A) Competitive areas drive up cust acq costs - avoid!
B) Spend a lot of time figuring out how to get your payback period to be on 1st txn when bootstrapped
C) Increase the value of your cust to make this work; there's only so much you can reduce CAC

18) If you get lots of reps on this, you will get better at spotting opportunities - either for yourself or to invest in.

But you need to try a lot in order to get exp. (Another reason to think in terms of portfolio construction in one's own career)

Practice applies everywhere

19) Having the right team makes a world of difference. Not just in whether you get along or not. But also in culture and skillset.

I LOVE working on @HustleFundVC because of my team.

20) First skillset - when I was in my 20s, I was pretty cocky (internally) that I could do a lot of things. To good extent, that's impt as an entrep - have confidence in learning new things that need to get done.

But don't let that get in the way of finding ppl BETTER than you.

21) E.g. in building out @HustleFundVC I can talk to founders and prospective LPs. I can communicate well with ppl.

But @ericbahn and @shiyankoh are WAY BETTER at it. They have the polish and ppl skills that I don't. And I'm ok w that.

22) We think like a sports team.

I "bring in" a lot of initial "leads" for LPs or founders because of my tweetstorms or blog posts.

But @ericbahn goes & closes them. I know it would be way harder w/ out @ericbahn & @shiyankoh because they are way better at this. Team effort.

23) Culture is also impt. We have had the chance to potentially woo a lot of baller people onto our team. In fact, we are constantly scouting for the future even if there are no openings today.

But, it's not good enough to have amazingly talented ppl.

24) For us @HustleFundVC, anyone who works here has to be humble and a nice person as first and foremost. That itself filters a lot of ppl out - hah.

Have entrepreneurial experience in some form - ideally as a co-founder.

And not take oneself too seriously.

25) Culture isn't about ping pong tables or video games.

Culture is about what your customers or wouldbe customers see from the outside when they meet an employee.

If we have 1 asshole @HustleFundVC, that would ruin the brand. No matter if they pick unicorns.

26) A good test of whether someone fits the "culture" is if you introduced that person to your customers, would your customers LOVE that person?

Not tolerate that person. But LOVE that person.

27) It's really HARD to find ppl who both represent your brand and are also highly skilled (and are available and want to work with you!)

This is why we spend so much time scouting potential recruits for the future.

28) @HustleFundVC is my last startup in my personal career portfolio construction. (No pressure!)

Looking back, I laugh at all my missteps earlier. They were part of the journey.

29) Lastly, we have a lot more to build & are just starting.

But if you still LOVE your team 3 years in & you have some semblance of PM fit - your customers love you & you have some repeatability, you've got something special. Hold onto that & don't let that go. That's the 1.