Opinion
Wilkinson: Things creator has 'won' more than Asana founder Dustin Moskovitz
“I am generally much more in the camp of the things guy has won, not Dustin Moskovitz. Dustin Moskovitz is just playing a different game than the things guy.”
Insight
Wilkinson: Leaders should fire an employee immediately upon first considering it
“And the kind of heuristic I have is if I ever think, should I fire this person even once I should fire them immediately. It has always been a signal, at least for me, that when someone's a superstar, I can't imagine firing them.”
Insight
Wilkinson: Hire fully formed talent for current needs rather than potential
“So I'd say like the lesson really is hire for what you need. Don't hire just for potential, which is counter to what a lot of people say. A lot of people say hire for potential and coach them into being whatever you need. I just haven't found that. I think you…”
Prediction Not checkable as stated
Wilkinson predicts AI agent 'iPhone moment' within next five years
“And so I think that if it was accessible to everybody in terms of, if you could just open chat GPT and say, Hey, ChatGPT, I run a business. Can you help me? And it started asking you questions and it said, oh, well, you know, you do sales. Do you want me to se…”
Opinion
Wilkinson: Teaching children how to code is becoming obsolete
“So now teaching kids how to code is like teaching kids basic and we have a GUI, right? You don't need to learn punch cards and basic programming because, or MS DOS, because we all have keyboards and mice. We don't have to do that. And I feel like coding has re…”
Prediction Not checkable as stated
Wilkinson: Prompt engineering will become obsolete as AI elicits intent
“And I think now people are saying people need to learn how to prompt, which I think is very true for the tool set right now, but I don't know how relevant that is in the future because I think we're still, again, in the palm trio phase. I think that the AIs wi…”
Insight
Wilkinson: First-time founders should start small instead of building complex AI or banking startups
“I don't necessarily think it has to be something that is small forever, but it has to be something that like, I think about if you're a first time entrepreneur or a student or something, you don't want to walk into the gym on day one and try and deadlift 300 p…”
Insight
Wilkinson: Founders must adopt 'lazy leadership' and shed disliked tasks
“So I think a lot of people have this kind of Protestant work ethic. Where they think, well, I've got to be the person to do everything. And I think they really need to lean into what I call lazy leadership, which is how do I get away from the things I hate as …”
Insight
Wilkinson: Focused Software Companies Can Scale to Hundreds of Millions Without VC
“If you're wanting to just tinker and solve a problem that you think is not going to be hyper competitive. So for example, that form filling thing or software that just does a narrow thing that doesn't require 20, 30, forty million dollars to be lit on fire bef…”
Opinion
Wilkinson: Everybody hates Salesforce, but switching is too painful to bother
“An example might be Salesforce where no one wants to, they've spent years and they've done all the implementation and trained everyone on it. And it's kind of the standard. Everybody hates it, but ripping it out and switching is such a pain in the ass that the…”
Insight
Wilkinson: Acquired company CEOs will only execute their own preferred playbook
“And I've just found that hiring CEOs is like, you're, they're an elephant and you're the rider. They're going to go wherever it is that they want to go. And so listening incredibly carefully to people's words and their experiences, because generally people wil…”
Insight
Wilkinson: Replit replaces a five-person team for my web projects
“So what I'm finding is that things that previously would have frustrated me because I would have had to rely on a team of five. I can just do entirely on my own when it comes to web projects and stuff like that.”
Insight
Wilkinson: Finding uncrowded niches is key because competition compresses margins
“And I think that's probably the most important thing in business is actually to find those niches where you can actually make real money because competition equals lower margin. The more competitors there are, the lower your prices have to be and the more comp…”
Assertion Not checkable as stated
Wilkinson: Film investors lose all their money 90% of the time
“And I realized that when you fund movies, like, 90% of the time you lose all your money. And even if you do make some money, you rarely make a good return.”
Opinion
Wilkinson: Letterboxd possesses a strong network-effect moat
“And I met the founder of Letterboxd and I realized, oh my God, this is a business where this has a moat. So it has a network effect. It's a huge social network for film reviewers.”
Insight
Wilkinson: Marketing freelancers should target wealth managers and realtors over restaurants
“And I said, well, you know, if you just pivot that idea just ever so slightly, And instead of doing restaurants, you did realtors or wealth managers who have quite a large marketing budget and are used to spending serious money. And it only has to work a littl…”
Disclosure
Wilkinson: Bootstrapping Flow against Asana cost me $10 million
“And I ended up losing ten million dollars trying to compete with venture-backed businesses and bootstrapping. It was all my own money, poured ten million dollars, lit it on fire, trying to compete with Asana because I didn't understand how the business world w…”
Opinion
Wilkinson: Enterprise SaaS is definitely easier to build than Instacart or Amazon
“Would it be easier to start Instacart, Amazon, or Coupang, or would it be easier to start an enterprise SaaS software company? Definitely the enterprise SaaS software company.”
Assertion Supported
Wilkinson: Tiny Generates Nearly $300M in Revenue Across Bootstrapped Portfolio
“I mean, we bootstrapped the entire business and now across all of our companies, we do almost three hundred million dollars in revenue.”
Assertion Partly supported
Wilkinson: Serato is the world's largest DJ software company
“So Serato is the largest DJ software company in the world.”
Assertion Not checkable as stated
Wilkinson: AI agents completely automated my email, replacing full-time assistant
“And I'd say that it's replaced stuff that my full-time, I used to have a full-time assistant just working on email. That's all completely automated.”
Prediction Held up
Wilkinson: Wearable AI Will Automatically Populate To-Do Lists and Emails
“And so eventually I haven't gotten there yet, but eventually you'll be able to just have it record your entire day and then automatically go into your to-do list or whatever it is and add to-dos or send emails or whatever you need it to do.”
Disclosure
Wilkinson lost billionaire status following decline in Tiny’s stock price
“At one point being worth over a billion dollars, by the way, should redo the title of the book from barista to billionaire. Now it's former billionaire because our stock went down”
Disclosure
Wilkinson: Taking an SSRI improved my mental state more than wealth
“No amount of money or success or attention or anything else had done what this little tiny yellow pill could do for my mental state. And so now I've been on an SSRI for four and a half years or something like that.”
