The Next Next: Update #15
Riding the roller coaster.
For those of you tuning in for the first time, The Next Next is a ‘build in public’ type of journey from founder Jason Jacobs (me!) to explore 1) how I can build my next company differently (prioritizing health and family, not just work, while still building an ambitious and important company) and 2) how AI can help, and more broadly, how it will change how startups are built and funded.
There is this newsletter (subscribe here), which publishes weekly and chronicles the ground I covered that week, insights I’ve gleaned, topics I’m wrestling with, and where I plan to dig in the week following. And there’s also this podcast, which publishes twice a week, and explores these topics in-depth in a series of interview-style discussions with others who are well placed for me (and you!) to learn from.
The goal of this public learning journey is to have it evolve over time from a journey into a livelihood, to prove to myself and others that it is possible to ‘have your cake and eat it too’, and to help define a new playbook for how to build companies that inspires many other founders to follow suit and gives them a roadmap for how to get started.
If you want to catch up, the historical weekly updates are here:
Week 1, Week 2, Week 3, Week 4, Week 5, Week 6, Week 7, Week 8, Week 9, Week 10, Week 11, Week 12, Week 13, Week 14
______
Another week gone by. They are flying!
These weeks are definitely up/down. Parts of every day I feel like I have the wind at my back and am heading down a fertile path, and parts of every day I feel like I am swinging in the breeze. From a big picture standpoint, I am exactly where I want to be. The hardest part is just managing my own psychology along the way! I find I am reminding myself frequently that this is how the earliest stages felt in every new venture I have ever started.
Relatedly, one thing I am wrestling with is building vs learning. Going wide and investing in learning up front is something I fundamentally believe in - especially in an emerging space like this one. But at the same time, I am super impatient to build. I do feel some personal financial pressure, so I am sure that is part of it. I am trying to block that out though, so I don’t over-optimize for the short-term at the expense of the long-term. The life of an entrepreneur!
I am also all over the place in terms of what is getting me excited. I am hesitant to anchor too early and ending up regretting it, so once the thrash naturally starts calming down and I am anchoring within a narrower and narrower band, I will know I am on the right track. If I am still saying this in my weekly updates several months from now, I may need a little push, but I am confident the fruit isn’t ripe yet.
Given I have been grinding myself pretty hard, it is good timing that I headed out this week on a vacation with my family. I am going to try to work for a few hours each day, but it will also be good to clear my head and step away from it for a bit.
In no particular order, here are some things on my mind this week:
Where to anchor
I think one thing that makes it hard to anchor right now is because it is still early innings and so much is in flux. I mean, I would not want to be an incumbent SaaS vendor right now. I also wouldn’t want to be an established firm trying to figure out how to incorporate AI into an organization that otherwise wasn’t built for it. I am glad to be at ground zero, with no technical debt, team debt, etc, that can build a truly AI-native organization from the ground up.
But at the same time, there is so much uncertainty. Even for the folks building from the ground up, the landscape is changing so quickly under their feet that it feels unsustainable to try to keep up. I am sure things are bubblelicious as well (false product/mkt fit, raising at inflated valuations, etc), so while I have no doubt we are in the early innings of a profound rewiring, I also don’t want to get caught up in the hype.
How ambitious am I?
This is also something I am struggling with. I have talked about how I am just as ambitious as my younger self, but instead of 100% of it allocated professionally, it is 1/3 to health, 1/3 to family, and 1/3 to work. And I believe this. But at the same time, I worry that by making that balance core to my journey it is shutting me out from being one of the people shaping the future direction of the world. When a wave comes, you don’t catch the wave by paddling with 1/3 of your energy. You do so by paddling as hard as you possibly can in a compressed period.
The above is certainly what I was conditioned to believe my entire career. I am continuing to pressure test that, as it is not realistic for me to put work over everything else in this phase of life and it is also not realistic for me to get excited about something that doesn’t feel quite ambitious.
Some ideas I am excited about
The fund I talked about last week still could make sense longer term, but I am not ready to rush doing that or doing anything. I will tuck it away though, as it is a path that could make sense as TNN evolves.
I continue to be excited about fitness. It is such a huge part of my life, and I spent almost a decade in a past life building a fitness company. It is a tough category to innovate in, and I still have PTSD from the last time, but gosh, am I passionate about it.
I am also excited about the idea of training AI models to do what only humans used to be able to do. This could be coaching. This could be teaching. This could be doing analysis. I started out looking at this for hockey coaching (analyzing player shifts and making recommendations for how to improve them), but this type of innovation could be applied in many areas. Basically, anywhere a human used to look at your form, positioning, etc and give feedback, I suppose you could train an AI model to do it. Not as a replacement, but to open up the market to many who either couldn’t afford, couldn’t justify, or didn’t have access to the human equivalent. Could be for learning viral TikTok dances, could be for learning trades like plumbing or carpentry, could be for analyzing your golf swing - the list is long and promising!
There is one idea I have specifically been noodling on within the above. Topgolf is cool because it is part utility, part fun. I don’t think many serious golfers would train there, but novice golfers can get better there, and it is also great entertainment and fun. If you look at the existing digital golf training tools, it seems many are focused on the more serious golfer. It seems there is an opportunity to essentially enable a Topgolf-like experience from your backyard with a club and a smartphone - no other gear required. Part game (badges for milestones, streaks etc), part Strava-like competition and challenges, and part coach. I am a long way from anchoring here, but I am going to spend some time on it, as every time I dig into an area, it moves the ball forward on my learning. In fact, this week I built (yes, built myself!) a working mini-MVP where you can upload yourself swinging a club and get AI-powered analysis.
I continue to be drawn to the small team, ambitious work, and flexibility/control model. That’s super vague and could be applied in any number of ways, but that criteria does feel like a constant in my search. Small team, AI-native, huge leverage, and lots of flexibility/control.
New content this week
Two new episodes out this week!
One is with Scott Weller. Scott is a multiple-time founder who is now neck deep in launching a new venture, which is building AI Assistants for bank and private lending origination, underwriting and portfolio management teams. They also have a fleet of agents in-house writing production code! Great discussion about launching new companies, building with AI, and how to break the chicken/egg when selling into big banks as an upstart. Episode can be found on Spotify, Apple, and YouTube.
The other is with Uday Chandra. Uday is one of two co-founders of a new venture that is building an adaptive business operating system (with AI and open source) to replace dozens of SaaS tools instantly in SMBs and emerging startups. Two person team, three months in, five paying customers, $45k MRR, no outside funding, and a growing AI agent army writing code. Too early to tell how this plays out, but this is one to watch! Huge if it works. Episode can be found on Spotify, Apple, and YouTube.
Focus this coming week:
Rest, run, family time, read, maybe write a bit (No meetings! No pod recordings!). Should be a quiet, reflective, regenerative week!
People I want to hear from:
People building ambitious, truly AI-native companies from the ground up.
Computer vision experts, data scientists, biomechanists, and good consumer product/engineering/UI people who are interested in providing feedback on the golf idea above as I move it forward.
People sitting on large piles of human movement video in a given category that may be interested in training models on it or licensing it for others to do so (or even better, people that have done this already!).
Experts in a given category (hockey skills coaches, carpenters, etc) who may be interested in helping train AI models to do the analysis or teach their craft to others, and explore what’s possible.
Lastly, a screenshot of a tweet that got me fired up. Abundance mindset, FTW!
Have a good week, everyone. Thanks for listening.