In the late spring of this year, I was in yet another existential crisis as a startup founder. My co-founder and I were in the process of rebranding our startup from Nessle to Parentswarm (thanks to trademark threats from a terrible bully of a chocolate company whom you should boycott). We were long since out of money. We were seeing some growth but certainly no hockey stick. We had days of encouragement when we could keenly feel the value of what we’ve built and are building, yes… but we struggled to monetize exponentially, grow quickly enough, or garner investment.
Michelle got a full-time job. I started applying for jobs. We have kept our startup alive, because there are users, it’s self-sustaining financially, and we see enough signs of potential that it’s worth it to us to keep the boat afloat, especially if it only takes a few hours of our time each week to do so.
But it doesn’t afford us any salary as founders.
So, back to spring: I was trying to figure out my next chapter. And I happened to listen to Episode 1937 of one of my go-to podcasts, This Week in Startups with Jason Calacanis. This particular episode, “Ask Jason LIVE!: Navigating startup growth with Real-Time Q&A | E1937,” kicks off with Jason offering career advice to a (failed) startup founder who sounded a great deal like me: former founder Dustin asks, “I just shut off my startup after about 3 years of working on it…but I’m struggling to find roles that fit the more generalist skillset I’ve developed over the past 3 years, and going beyond that, knowing how to market myself, because a lot of companies are looking for specialists. So I was curious if you had any advice on where to look and how to pitch myself.” Jason proceeds to counsel Dustin, a “Jack of All Trades,” to lower his personal burn rate and spend a dedicated, focused time developing his perspective and brand as a “customer discovery engineer,” to spend 30 days putting out thought pieces / blogs centered on on his superpowers, his most marketable skill, his strongest area of expertise. For 30 days, Jason advises, “I just want you to create content about customer discovery and what you’ve learned. And I want you to highlight other people’s learnings and what you think about them… Now you’ve established yourself as a credible expert on this topic…come up with your own thesis and playbook, and then, after 30 days of this, you find 10 startups that are in the seed stage…and you say: ‘hey, I really think what you’re doing is interesting. I’m a former founder myself, and I am an expert on [x]. I’m wondering, looking at the customers you have, if you need help with this. I charge reasonable rates, and I’m passionate about startups. And you can book a 20 minute discovery call with me on my calendly link here.” And then you essentially become a freelance consultant with the potential to be brought on as a co-founder or an early core employee at a startup you admire.
This was Jason’s advice, and I thought it sounded exactly like something I should try myself. So that’s what’s up for the next 30 days. I’m going to put out regular content–via my WordPress blog–that’s focused on customer experience / user insights (my superpower) along with a few adjacent nuggets about the things I’ve learned over the past few years as a startup founder. My writings will be raw, genuine, and in my own voice. I can promise a clear perspective and honesty that goes beyond what you can expect to read in most content mills or phoned-in LinkedIn posts. Will anyone read it? Maybe. Maybe not, but hey, it’s an experiment, and Jason told me not to worry about that. So here goes.
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