3) Mindset

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Introductory Remarks

Dear Vambracers —

In last week’s post, Let’s Get #Technical, I went deep into my current tech stack and provided more general thoughts on my experience with those tools, how I elected to use them, etc. I think the overwhelming feeling throughout this journey has been one of agency and empowerment—and that really has been made possible by my tech stack. #thankyousam! (and Dario)

Mindset

Today I wanted to explore my mindset as I embark on this journey—and try to identify some of the foundational psychospiritual principles that I hope will root me and my work, and my approach to the day-to-day rhythm of the journey. I think it’s particularly important to explore this area of the entrepreneurial journey so early in the process because, really, mindset is pretty much all that I have.

Overthinking is the enemy

I was listening to an interview with Christina Cacioppa the Co-Founder & CEO and she talked about how she thought a lot of people talked themselves out of starting companies because they thought too much. And I think that’s definitely been true for most of my lived professional experience and then also something that I’ve observed in others I’ve encountered as an investor. It’s so easy to build a unicorn, and to prove all the haters wrong, and silence the doubters, and give ted talks, and be interviewed by Garry Tan in your head. But really thinking alone is not sufficient for any actual impact in the world. I know that seems obvious but I think it’s often overlooked.

I think the related point that I’m trying to drive home here is that, it’s so easy to get caught up in all the permutations and simulations and challenges and battles of the future that you forget to take concrete action in the short-term. Because I’m sure that 99% of the imagined future battles that you’re gearing up to fight will probably never happen. So I think I have to condition myself to almost not think and just to keep moving things forward—each and everyday—even if it feels small or insignificant or whatever—anything is better than nothing. And the danger I think is that thought can really feel substantive and productive when really at best it’s not constructive and at worst it’s actively destructive to future goals. So I think that’s a core pillar of my mindset heading into this endeavor.

There’s a million reasons to not do something

In a similar vein to overthinking, there will always be a million reasons not to do something. And by definition starting a company or pursuing an entrepreneurial endeavor is highly risky—and risk really stems from uncertainty. And so with anything that you want to do that it risky and uncertain, there’s an abundance of reasons—and good reasons at that—not to pursue something. This is where another mindset shift has to happen around downside mitigation vs upside pursuit—and this is also something I learned as an investor and something that I think Bil Gurley talks about a lot: it’s easy to focus on all that could go wrong, but really you have to ask yourself, what if something goes right?

And so to be somewhat concrete here within the context of my journey, I’ve had internal conversations (with myself) around, yes, this is crazy, and, yes, there’s a good chance this doesn’t work—BUT, what if it does work? And even if I fail what if I learn a lot in the process? And what if I learn a lot about myself? And so then I think the conversation has become more around, sure there are a million reasons for me not to do this, but what are the 5 reasons why I should dive into this pursuit headfirst? And if I can get absolute conviction around like 5 reasons (which I think I have, although I’ve never like formalized those reasons), then I think it’s a worthwhile pursuit. More generally, if we always focus on risk mitigation and squeezing uncertainty out of the future I think we’d just be compelled to remain complacent and to embrace the status quo or pursue modest stepwise improvements in our lives. And I’m trying to take giant leaps. And, sure, I’ll probably miss the mark more often than not—but I also might not. And the leaps I land, I think, will make all the leaps I don’t land worth it.

Control what you can control

Shifting gears a bit, another core pillar of the mindset I aim to espouse is to focus only on what I can control, each and every day. It’s important to be aware of the broader business environment and do proper diligence around competitive solutions and so on and so forth—but I still can’t let the actions of competitors or other exogenous things hamper daily momentum and continued progress on my end. There’s always something that I could be doing to advance the initiatives of the company and my being—and so I can’t let overthinking or the actions of others discourage me from continuing to take action.

Mike Tomlin says: “I never want you worrying about the people on the outside, even the man sitting next to you. This is a man versus himself battle. You have to be continually pressing to get better with that understanding that this is a highly competitive line of work that we’re in.”

That’s a similar attitude to what I’m trying to bring to this endeavor. It’s not about what other people are doing. It’s about what I’m doing to improve myself, to better serve customers, and to create a more cohesive, constructive, and productive organization (which, right now, is an organization of 1).

Is this constructive to my being?

In general, I’ve been obsessed with the concept of constructive vs destructive experiences. Another saying that really resonates with me is: “Whatever liberates my spirit and gives me mastery over myself is constructive. Whatever liberates my spirit without giving me mastery over myself is destructive.” And that can apply really to all areas of life and I think also any type of organizational development initiatives. How do we liberate the collective spirit of a group of people—including our organization and the organizations and customers that eventually use our product (hopefully)—in a manner that gives them mastery over themselves and is constructive to their being. I think spiritual liberation is really what many people are chasing after, knowingly or unknowingly, and so creating tools and experiences that allow individuals to constructively achieve spiritual liberation can really embed themselves in the lives of users.

Less relevant to what I’m specifically trying to build, but I think the most successful businesses of the past century or so have been built upon destructive spiritual liberation (and usually some form of addiction): social media companies, alcohol companies, cigarette companies, (more recently) gambling companies, etc. They’re profiting off of the destructive spiritual liberation of consumers and I think that’s why they’re obviously such good businesses. Because spiritual liberation is what everyone wants—and destructive spiritual liberation is easier to achieve than constructive spiritual liberation—and so it’s easy to get the immediate dopamine hits from these types of products and services. And they know that and are designed to exploit that. I’m not here to castigate businesses that exploit the fallibility and need for spiritual liberation of consumers—although I do think it’s horrible, to be clear—but I am here to promote constructive spiritual liberation and aim to align any future business success around some type of constructive experience for users that is additive to their being, even if in a small way.

And then within the context of my own life and entrepreneurial journey, I am constantly asking myself: is this constructive to my being? And so I think that’s the same type of heuristic that I want to embed within this organization. Especially with the rise of AI which increasingly will displace more menial and menial-adjacent labor (and I’m lumping white collar work into “menial”), I think the types of professional experiences that we pursue will change—and it may be more difficult to directly attribute some business outcome to an individual’s time and intellectual input. And so I think then there has to be a shift from: “did you drive ROI” to “was this constructive to you and our organization?” And I don’t really know how that will manifest itself over time—and honestly I could be totally wrong here—but I do really think that the nature of work and measurements of performance within an organizational context will have to change in the coming years.

I know I’m wrong, but why am I wrong?

As a relatively high-achiever throughout most of my life, it’s definitely been difficult to recondition myself to being wrong like pretty much all of the time as it relates to the initial conception and construction of our product—and I’m sure many future iterations of any product I aim to build. And so think cultivating an attitude of humility and resilience in the face of near-constant wrongness has been and will be important. And then, if you assume that I’m wrong like probably at least 90% of the time around what users want, what features are critical, etc., then really what becomes important is understanding why I’m wrong and how to synthesize wrongness into real insights around why, such that, over time, maybe we can from 90% wrong to like 60% wrong—and then I think you can build an enduring business on 40% right so long as those rights are significant enough in like impact to overcome the 60% wrong. And then even within this wrong/right framework, I’m sure there’s some like healthy level of wrongness that indicates an organization that remains open to experimentation and pushing the boundaries and exploring new ideas and stuff.

But, really, all I’m getting at here is that—as someone who tried to be right > 90% of the time on pretty much every academic endeavor I ever pursued—rejoicing in only getting things right 10% of the time and then deeply exploring all the reasons for my utter wrongness is a pretty jarring mindset shift.

Agency is the ingredient and action is the antidote

Part of the beauty of the entrepreneurial journey seems to be the immense amount of agency required to actual build something that resembles a self-sustaining business organism. I’ve always believed that pretty much all forces in the world push for maintaining the status quo—and so when people start companies with the goal of affecting some change on the world, even if it feels small, I personally believe that that’s one of the most noble uses of life (and this applies to entrepreneurship broadly across creative endeavors and business endeavors). And so basically embracing the intrinsic agency of existence to pursue change is incredible.

Within the more day-to-day rhythm of life, I think agency manifests itself in the form of being able to test things out, being able to reach out to people, being able to really become an active participant in the discourse of some esoteric-feeling subset of business problem or personnel, etc. Like if you have an idea—any idea—you can take that from idea to implementation in a matter of hours. And I think within formation-stage entrepreneurial endeavors, that bias for action and experimentation is critical to progress and momentum.

And then the related point I want to make here is that action is the antidote to fear, uncertainty, chaos, etc. If you learn about a competitor, you can exercise agency and take action to research that competitor’s offering, or to get back to work on your own offering, or your pitch deck, or whatever—and I think exercising that agency and taking action in the face of chaos and uncertainty is really important.

I’ve got no one to rely on except for me

And then the last point here, the beauty—and the danger—of the entrepreneurial is agency—because really at the end of the day there’s a fine line between building a startup and being unemployed (I think Parker Conrad said something like that). And so I think there’s a real sense of the buck stopping with me and like ultimate accountability and not having anyone to rely on except for me. Success or failure, especially in the early days, really is entirely dependent on me. And so our willingness to like pursue our ideas, and to seek feedback, and to become comfortable with discomfort, etc., is directly related to my mindset, and my aptitude, and my willingness to be told I’m wrong, and so on and so forth. And so really the buck does stop with me—and part of the reason that I’m excited for this next chapter is because, I think, that I’m someone who thrives in that type of high-pressure environment. I need to feel the heat to be at my best—and so I need to embrace this extreme accountability and responsibility—and acknowledge that I really don’t have anyone to rely on except for me—nobody is going to save me—and the secret is there’s no secret.

Looking Forward

That’s all from me for this week. I think next week I might write about challenges leading up to some launch and get a bit more concrete around longer-term marketing and user acquisition strategies—or something like that. Because I’m nearing the point where I need feedback-feedback-feedback—and I have to really cultivate the environment of wrongness that I just spoke about. And so I will report back on that journey soon

Have a great week! Rejoice in being wrong and pursue some constructive experiences!

Sincerely,

Luke