First, thanks for talking today.
Really loved hearing where you are.
After we talked, in my opinion, you should do one of two things:
Quit tomorrow and start your own company. It will be scary as hell, may not pay off, but could be super rewarding and educational.
Or quit ASAP and join The Hustle where you’ll help us grow our community, build a team that becomes a machine, help us launch new products and, and be a massive part a culture-changing brand.
Of course, there’s also option #3, which is staying put. I think we both have similar opinions on that one… you’ll earn a big-ass salary for a long time but will grow soft, fat, and, worst of all, complacent.
I’d avoid option #3 like the plague. Taking any risk after years of being safe is tough to pull off.
There are a ton of pros and cons for doing #1. I did it. You’ll be in charge of your own destiny, you’ll feel alive, and you’ll (most likely) have few regrets.
However, you will feel lonely, go through an emotional rollercoaster, and most likely won’t see success for a couple years. That’s part of the game though, so I don’t think you should feel discouraged by that stuff. You’re going to go through it eventually as you most definitely will start a company one day, it’s just a matter of when.
Now, onto option #2: joining The Hustle.
Like we discussed, I think there are a few reasons why you should do it:
- There’s little downside: In my opinion, The Hustle’s most likely worst-case scenario is that we grow very little and are a nice, profitable business that makes $5m a year in revenue for the next 5-10 years and kicks off a good little dividend. Honestly, that’s my nightmare and I’d rather go bankrupt than be mediocre and not grow. But, for you, that’s not that bad. You’ll always have a good salary, visibility (media companies are super public and everyone will know you were part of us), and you’ll learn how to operate a business since you’ll be part of the high-level decision making. And, if things suck and I don’t live up to my ambition, you’ll quit after 6 months and do option #3, #1, or get another high-paying gig somewhere else. Not bad, tbh. You’ll at least know what not to do when starting your company.
- You have the chance to be impactful: We have 14 people right now. We’re tiny. And, this position is a senior role. The plan is to have you get onboarded by John then manage a team that becomes a machine. Additionally, because we’re a media company that wants to monetize beyond just ads and we have yet to launch those new products, you’ll be part of the decision making the process to think of and execute new ideas. Sometimes, we have a new idea and execute on it that day. Other times it’s a week. Either way, we’re small enough to move super fast but big enough to have some resources (a dev, a little bit of money, and 2 more team members) that’ll help you succeed.
- You’ll learn a ton: And finally, you’ll learn a fuck ton. My co-founder and I know how to start something from nothing. We know how to make small but meaningful amounts of money, how to launch successful products with zero resources, and how to hustle like crazy. You don’t. We’ll teach you. But you know what we haven’t done yet? Scale from 1 to 100. You’ll teach us that, we’ll teach you the other stuff. You know how much John and me know about media? About 18 months worth. Practically nothing. Yet, we get asked to speak at conferences all the time. Why? Because 70% of the day we’re working on things that are totally new to us. We screw up a ton because we try so many things and are constantly in uncharted territory. That makes it easy to learn. You’ll be in the same category. You’ll help us understand how to create a $100m+ company and I’ll teach you everything I know about starting out (you’ll also learn as you go).
Anyway, those are my thoughts. Obviously, I think you should do #2. We have a stellar team but are missing your type of personality. But, regardless if you do #1 or #2, don’t do #3.
OK, so onto my offer. As I explained at the office, I can’t beat your salary. I can’t even come close. If you can find a 10-15 person startup who can and you’re passionate about it and they offer big upside, take it because that’s crazy high. Or hell, tell me about it. Sounds sick. We’re not on that level yet and have 14 other people to look after. So, while I want to give you what you’re worth, I can’t do it now.
That said, here’s what I can offer:
I can’t put a cash amount on the equity because I think it’s unethical and maybe even illegal, but you’re smart and can make some assumptions. Some companies like ours (Daily Candy) sold for $125m with 2.5 subscribers. Others are currently on the market (theSkimm) for ~$90m. And then there’s Thrillist, Vice, BuzzFeed, Business Insider, and more, that have exited for $500m+.
OK. This was long. Give it a think. Then, say “yes, I’m in” and we’ll settle on a start date and I will send an official offer letter.
I know this is a bit of a leap for you, but you only live once and now’s a chance to walk the walk.
Let me know,