Risk Early
Thinking About Advice I Got When I First Got Into Tech
I have a portfolio company launching on Product Hunt today (plz support if you feel compelled!). They are hustling their faces off to get upvotes and spread the word. I remember doing the same exact thing on my Product Hunt launch days. I stayed up until midnight for the launch and woke up at 8am to work the launch the full day. I DM’d every friend I had (and didn’t have), telling them to upvote us. I pushed emails to every email list that I had. I would fight tooth and nail to get to the highest spot. That’s exactly what I see these founders doing. And it’s working. They are number #2 as of the time of this writing. But watching them grind makes me think… if I were launching a new thing today, I don’t know if I could hype it the way I did when I was first getting started.
When I first got into startups, I got advice along the lines of: “go all in now — you’ll have the least risk and the most energy you’ll ever have in your life.” I took that advice and quit my job to go all in on a company called PubLoft back in 2017. By going all in on PubLoft, I was able to focus on scaling revenue growth of the marketplace. By focusing on growth and having a vertical revenue chart, we were able to get backed by Jason Calacanis. By being backed by Jason, I was able to experience the Bay Area life and seed my network up there. That is the basis for the work I do now. Without the accelerator, who knows if I’d be in tech today.
It begs the question: could I just do the same things I did to start PubLoft today? I don’t think so. PubLoft took a pure hustle and willing it into existence that I don’t know if I would have the stamina to do today. Sending hundreds of cold emails. Applying to every accelerator. Having no shame in my social circles. No shame at all. It’s just harder as a mid-career guy who does not have the “young” or “he has potential” card to lean on. And it’s far less socially acceptable to be doing those things being a non 20-something. Doesn’t mean you can’t, but it is a real dynamic.
Look — I’m a husband. A father, soon to be of two. And I just don’t have the energy to work a launch all day anymore. And even if I did, culturally I’m not able to. Unless I wanted to prioritize all of this activity over spending time with my family or working on my health, there just aren’t enough hours in the day the way there were 5–7 years ago. But here’s the kicker: these young-career people need to hustle that hard because no one knows who they are. They need to break in. They need to establish a foothold. They need to make a lot of noise to move an inch.
Me? I already did that, starting 10 years ago. So if I wanted to start a new company, I don’t need to hustle like an unknown 20-year-old hustles. Hustle for me looks different than just being high activity. I know more people, and I know more things. I just need to make a few calls to people I already know and make higher-leverage decisions that weren’t available to me seven years ago. But if I didn’t hustle the way I did back then, I wouldn’t be in this position now. If I wanted to start in tech today, I wouldn’t be able to repeat my same success. It was key that I started when I did.
Also, to be clear, me saying “I don’t need to hustle like I did back then” is how people like me get beat out by some young guns that want it more.
There is something about being young. Not really knowing how the world works yet, but having full belief that you are able to make a dent. And having all the time and energy in the world to try to do that. Very few obligations. Few headwinds. As you get older, it just gets harder. You have less time. Less energy. You need to worry about your own health. The health of a spouse or parents. There are many things that take away from the pure focus of being a 20-year-old grinding. You don’t expect these things to be an issue, but now that I’m on the other side, it’s a real dynamic.
If you’re reading this as a young person wondering how you want to plan your life, I would not assume you can just jump into startups in 10 years after you work a safe non-tech job. I would encourage you to either find a job at a risky, high-growth startup that has the potential to change your life, or start one of your own. My advice is to join one before you start one — but if you’re compelled to be a founder, go crazy.
As a 22-year-old who got the advice that I would never be this unbounded in my life, and now being a 32-year-old who does not see a path for how I would build a career in tech from scratch starting now, I cannot agree with that advice more. I can only do what I do now because of the time I put in when I could take the risk. So take the risk. Do something crazy. If it doesn’t work out, you have time to recoup. And if it does work out, you’re going to be able to capitalize harder and for longer. And at the very least, if you have startup or tech dreams, do not say you’ll do them in 10 years after XYZ. It only gets harder as you get older. So get started today.
This is such a mature position to have. It helps that you have both experience and a network, but it's the mindset that makes most of the difference. Less grind and more strategically deployed work and leverage.
Whenever I look in retrospect, I too get the same feeling, that I won't be able to duplicate the hustle. But, in a way, I think that I'll be able to see the forest much better, as I shift my focus away from the trees. So much of the work I did back in the day was in vain — both as part of inefficient processes, as well as failed startup experiments.
But one thing is for sure — it helps a lot to have continuity of narrative within an industry. I'm working on a startup in EdTech now, after years of doing affiliate marketing within the fitness industry, and running a fitness VoD platform. I did years of SEO contracting as well, which had me all over the place. It's a priviledged position to find one's calling early and pave the way. Luckily though, the skills and experience pile up either way. Enjoyed the read!