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- 11) Tacking
11) Tacking
When Mr. Market sends wind your way, what do you do?
Behind-the-scenes building Vambrace AI, a company on a mission to unlock the truth in human conversation. Please pardon the stream-of-consciousness style. Subscribe to follow along or visit the site here:
(typos are to make sure you’re paying attention)
Introductory Remarks
Dear Vambracers —
In last week’s post, Competition, I explored some core beliefs for how to think about competition in the earliest days of building. The biggest takeaways for me were: (1) it’s easy to let the looming threat of competition dissuade you from pursuing something, but so long as you’re self-aware and nimble you should keep moving forward; and (2) it’s hard to compete with me right now because I’m still not certain what I’m building—so how can somebody compete with something that isn’t yet fully formed?
Last quick thing: it’s also kind of encouraging because the more uncomfortable and challenging things get, and the more reasons there are not to do something, that actually serves to cull the competitive herd. And I think that’s life, in a lot of ways, you just have to keep pushing forward no matter how hard things get and when many others have turned around and returned home.

Walter on a solo sea sojourn
Tacking
Today, I’d like to explore the concept of tacking—as opposed to pivoting—within a business context. In the early-stage entrepreneurial journey, it’s important to interact with the world as much as possible—and really listen to what the world is telling you—even and especially when what you’re hearing is the last thing you want to hear.
As I’ve continued to interact with the world and talk to really smart people about what I’m building, it’s become obvious that my current solution is a “nice-to-have” and not a “need-to-have” and that’s just no good. So I realized this past week that I need to redefine the core problem I aim to address, albeit within the same customer journey (at least for now).
I’m not going to go into any specifics yet on the actual tacking maneuver, but I did want to explore the psycho-spiritual construction of a tack.
Let’s get #nautical.
Necessary Preconditions
A few quick things:
Interaction
I actually view realizing that a slight change in course is needed as a positive indication that I’m on some right path. I’ve said this since the very start, but it’s really important that I actually take what I’m doing and put it in the world, and then interact with people, and listen as thoughtfully as possible to what they say. [Ironically, I’m using my platform to analyze the conversations that I’m having.] But it would have been much easier to kind of hole up and just continue to build and build without actually telling people about what I’m doing or having people try it or asking smart people in the space what they think. And that’s how we can get feature-creep and solution-centric building, which would probably lead to lack of traction and de minimis demand. So, it’s a good reminder to keep interacting-interacting-interacting especially when I least want to.
MVP
I’m so thrilled that I was able to build and launch my MVP—flaws and all—because it’s actually something real that people can interact with and observe and play with. And I’m realizing the possibly-obvious truth that that’s the real value in an MVP. It’s not building something that actually solves problems for customers (although that’s of course the goal!), but it’s more so having something real that people can play with, which hopefully kicks them off on their own imaginative journey-of-what-could-be. And then listening to where they go on their journey-of-what-could-be becomes the really important and interesting thing. And then once you collect enough journeys you can sort of line them all up and see if and where things overlap—and then modify the product accordingly.
Good faith market participation
I do think a big part of this entire iterative listening and learning journey is being a good faith participant in the market discussion that you want to be part of. I’m really listening, and really trying, and really working to understand what people experience and the problems they face—and I hope that they can feel that in our interactions. Because I think that engenders some subconscious belief in what I might eventually be able to build, and then that’s how you collectively birth a real product that solves a real problem for real people. And that really is the true North Star of a pre-PMF company.
Tacking Tactics
I’m like mid-tack, so take all of this with a grain of salt. But here are some of the winds I felt that made me eventually accept that a change of tack might be necessary:
Repetition
The more you speak with people, the more you can start to identify patterns in thinking and speech that surface, and then those patterns can start to inform a better sense of how “the market” is reacting to what you’ve built. I think it’s human to question the generalizability of individual feedback at first, and then once you talk to a sufficiently large number of people (maybe 10-20) then I think you can honestly start to pick up on legitimate patterns that are indicative of the market’s opinion (right or wrong, btw). This allows you to make an independent assessment of market sentiment, which requires self-awareness and brutal honesty. It’s possible that you can listen to the market, and reject what it believes. Or you can listen to it, and agree. In either case, the important thing is the listening. But this is all made possible by repeat interactions across a sufficiently representative population of individuals.
Modification
It’s less about completely changing my approach or some of the fundamental beliefs that inform this pursuit, and more about modifying the technical application of my fundamental beliefs to better serve people. And I think all of this knowledge accumulates over time, so it’s all part of the journey, which in retrospect will probably be more linear in subtle ways than it might feel right now.
Idea space / maze
The concept of an “idea space” or “idea maze” is pretty well trodden within the startup ecosystem—but it’s fun to actually be running through that maze. I’ve actually started to think of this entire process as sort of like a video game, and you’re doing little quests over time and learning about the map and building a catalog of the characters involved in the construction of the game’s ecosystem. And then you see competitors and opponents maybe at more advanced stages of the game or something, and you take note of their approach. And then over time as you collect more information, you start to maybe see why they’ve made certain decisions, or why they’re approaching things a certain way. And so it’s almost like unlocking nuggets of knowledge that others have already unlocked. And it’s actually kind of comforting or oddly reinforcing in a weird way because it means that you’re actually on the “right” path. And then I think the nature of competitive development with a startup ecosystem is that, the onus is on me to find an undiscovered path or meet an undiscovered NPC who shares some nugget of wisdom that lets me discover a different course that more quickly leads to the “boss” or something. But what I really want to drive home here is just how fun it is to kind of be in this massively multiplayer online game of an idea space with the world.
People say what they want
People mostly will tell you what they’re thinking and what they’re feeling—if you create an environment of trust and kindness and encouragement. And so it’s been great to just talk with people and ask them about themselves and their lives and learn what they’re feeling and what they’re struggling with and then going from there. So I really just need to keep talking with and listening to people.
But I guess the point I’m trying to make here is that all of these activities and behaviors have helped me arrive at the need to tack a bit—and then we’ll just keep repeating this process over and over again until I build something that actually “works.”
I won’t let myself die without having experienced real honest-to-god product-market fit. I just won’t let it happen. I will not breathe my last breath without having experienced exponential demand for a product or service I’ve built.
Learnings
Gut feel
This is probably the case more broadly in life, but you can feel certain things in your gut before you actually allow yourself to accept them. And the current tack I’m considering had actually been surfaced to me probably like 2-3 months ago, and I sort of chose not to think about it too much at that time—which I actually think was the right move. But really I’ve been feeling the headwinds since this journey first began, and I’ve only just accepted that I need to adjust course to accelerate my boat.
Hard means very hard
One general belief in the startup community around AI is that, as AI continues to penetrate society, we’ll be able to work on much more difficult things—and I think that’s definitely also true within the context of building a company. I can’t just solve surface-level problems that honestly are kind of easy to solve when there are much more pressing and challenging problems out there. And I think there’s probably some world where you play on like a difficulty-of-problem arbitrage whereby your target market doesn’t realize that you can solve their problem in a somewhat-easy fashion, and maybe that’s really the best product-market fit or something, and maybe that’s also like the entire equation of startups, because you’re exchanging your insights and know-how for capital to some target group. But, whatever, I still think that there are a ton of really really difficult problems in the world and that I need to actually swim into choppier waters.
Sunk costs in the sea of customer pain
A difficult reality of tacking and shifting strategy and trying new things as you learn more about the market is feeling like what you’ve already done was really for nothing. This is a pretty perfect application of the sunk cost fallacy, and I think living it is definitely different than learning about it—but it still holds true. Everything I’ve done in the past 3 or so months has put me in this position and has helped me build a much deeper understanding of the market and products out there and what people are interested in—and so really there are sunk costs for sure, but the endeavor has been net-positive and constructive in the aggregate to my soul and to the company—and that really is my North Star in this arena. There will always be mistakes and time lost to folly, but it’s important that I don’t let myself lose any additional time by wallowing and regretting. I just have to keep moving forward and being thankful for another day and another opportunity—and being grateful that I can keep moving forward. But this is an example of the psycho-spiritual challenges associated with the entrepreneurial journey, and it’s easy to beat yourself up over it. But it’s also live, and you just have to keep on pushing.
Problem-oriented means criticism isn’t self-indictment
Possibly the most important consideration associated with this entire shift in strategy and headwinds from the market is that the winds actually don’t really care at all about who you are or the boat you’ve built. And that’s not to say that the people I talk to aren’t interested in who I am and stuff—but really it means that it’s not like winds of the market are rooted in malicious climactic shifts or whatever. They’re not trying to make me adjust course or force me to abandon ship or whatever—they’re just blowing, as winds tend to do (literally by definition). And so it’s nothing personal, and it’s not an indictment on me or my character or anything. How could it be? Market dynamics are natural economic and societal phenomena, and so there’s no use pitying myself or playing the victim as I experience the natural gusts of life.
Boat metaphor aside, that’s why it’s so important to remain flexible and problem-oriented throughout the pre-PMF journey. It’s not really about me at all and it’s entirely about understanding a certain customer, the market that consists of the collection of those customers, and the problems they face. If I ruthlessly and relentlessly focus on listening to people and the challenges they face then the solution will hopefully become obvious over time. But I can’t lose sight of what really matters, and I have to make sure that I never put the cart before the horse. Demand drives product-market fit, and demand comes from problems that real people experience. I just have to keep talking, and listening, and being curiosity-driven and I will hopefully stumble my way into some paying customers and a real business.
Looking Forward
Some difficult and uncomfortable realities to face. But I also think when you feel like you’re pushing against a string it’s really not the worst thing to take a big step back and reconsider all possibilities. And I think my core focus around text analysis remains unchanged, and my current solution even could end up still playing a role in where I end up. But I think it is a good time to explore some other problems, markets, and areas for me to apply my enthusiasm and interest and energy. And that’s a natural part of the entrepreneurial journey I think.
The only way to find out is to live it—and I’m sure doing that as best I can! Have a wonderful week! Don’t let your ship sink!
Sincerely,
Luke