Decisions

Are our decisions ever our own? Is Gandalf the greatest entrepreneur in fiction? How do you know if you’ve made the right decision? I seek answers to these questions.

For most of my life, my decisions felt like they were mine. I felt I was on a path of my choosing. In recent years, though, I’ve realized I haven’t been moving towards anything, but away from something else: a feeling of insecurity; the feeling of not being safe; the resulting emotion from having to add up all the ones in my wallet to see if I had enough for lunch—or sometimes, if I had enough for guac on my Chipotle burrito; the disappointment of being cut early at my restaurant job that I was using to pay my way through college, at $2.13 an hour—after driving the 30 minutes, opening the whole restaurant, and doing my side work. This was not a casual revelation, but a result of a journey, and an attempt at finding some sense of “freedom”.

These struggles are the paradox of existing and of adversity, which are frequently synonymous. These circumstances I found myself in felt like obstacles, but also created the branching paths of my life. To be clear, the obstacles along my path have always been mild; I may have been poorer than average growing up, but that’s the worst of it. They left their mark, despite their superficiality. These feelings of restriction, constriction, and limitation planted a seed of deep dissatisfaction for me in any perceived lack of agency in my life. It pushed me to strive for more, to pursue higher education, and to figure myself out. And after all of that, they led me to consider an alternative path. In many ways, my journey so far has been clawing my way up Maslow’s pyramid. Considering my life path in this light strikes me with a sense of sonder.

Robert Sapolsky, a Stanford professor and author of “Determined: A Science of Life without Free Will”, writes:

You cannot decide all the sensory stimuli in your environment, your hormone levels this morning, whether something traumatic happened to you in the past, the socioeconomic status of your parents, your fetal environment, your genes, whether your ancestors were farmers or herders. Let me state this most broadly, probably at this point too broadly for most readers: we are nothing more or less than the cumulative biological and environmental luck, over which we had no control, that has brought us to any moment.

This idea nearly gives me an anxiety attack. While some may find surrendering their agency comforting, the very foundation of my psyche rests on the idea that I have agency. But despite the discomfort of this idea, it is still worth considering: have we ever really decided on anything? Can we? Isn’t the basis of our being, our very ability to decide? “Cogito, ergo sum” and all that.

Then again, “free will” also happens to be the stock answer to the problem of suffering by some world religions. Maybe free will is bad. Maybe it is simply an illusion. Maybe I should not have built my psychological safety upon its shaky foundation. I’m no philosopher, so I’ll set this consideration aside for now, and defer to the expert on willpower and getting shit done: Gandalf.

Gandalf seems to think our will really is all we have:

I wish it need not have happened in my time,” said Frodo. “So do I,” said Gandalf, “and so do all who live to see such times. But that is not for them to decide. All we have to decide is what to do with the time that is given us.

“All we have to decide is what to do with the time that is given us.” This is the very definition of “will”. Deciding what to do with your finite amount of time. If you were one who craved and cultivated this idea, entrepreneurship would be a particularly enticing idea.

I am one of these people; for the past 15 years, I have been devouring every piece of media regarding entrepreneurship: How I Built This, Indie Hackers, YCombinator, Shoe Dog, The Embedded Entrepreneur, The Mom Test, and countless other books, podcasts, online communities, and essays.

I have been pushing in the opposite direction of those feelings from my youth. I have convinced myself the only path to true freedom in a capitalist society is one of financial freedom, and entrepreneurship is the quickest way to financial freedom, according to all the success stories. Like Paul Atreides in Dune, I see thousands of futures and this is the sole path forward. Earning a wage, being an employee, climbing the career ladder—these feel like shackles, and I will be unshackled. This overzealousness is an entrepreneurship pre-requisite, right?

Setting out

In March of 2022, I decided I had heard enough of Guy Raz telling other people’s stories. I wanted in on the action, but I felt directionless. I had dreamed up some big ideas, and even attempted a few small projects on my own, but I needed a Sam to my Frodo. I posted on the Indie Hackers forum, in a “founder seeking co-founder” thread.

I talked to a few groups of other founders, but immediately felt a kinship with one in particular. A man named Ian, who had worked in a startup before, and was confident, amicable, and clearly competent. Ian lived half a world away, but we connected, and had complimentary skills, and our connection was the much needed spark to kick off the journey.

In a lot of ways, finding a co-founder is a lot like dating. To start, we both filled out a “dating questionnaire”. Here are a few of my answers that I found kind of interesting:

What are your strengths and superpowers (beyond functional expertise)?

My ability and interest in exploring a range of interests coupled with my ability to synthesize new information quickly has helped me grow a powerful skill-set for tackling business challenges. Others have mentioned my speaking ability, that I am “wise”, and that I am funny.

What are your weaknesses? How do you try to compensate for them?

I don’t have in-depth knowledge in any particular area. I’m an extreme generalist. I compensate by being a quick learner and by being willing to fail. I sometimes suffer from the stereotypical trappings of being a white male engineer: overconfidence, staunch opinions, directness. I try to overcome that through persistent and practiced open-mindedness and empathy. I also am too dependent on external validation.

And one more that is a little too relevant to the discussion of how we decide, and if we even can:

How do you arrive at your convictions? What are some key mental models you use to be creative, solve problems, or make decisions?

This is a pretty deep question. I’m not sure how I arrived at my convictions. I suppose the same way that everyone else has: a summation of all of my life events, experiences, and interactions.

One school of thought I tend to appreciate for this is Stoic philosophy (Seneca, Epictetus, Marcus Aurelius). I’m not particularly religious, so I tend to really value time and experience above all else. I want to make the most out of every day. I tend to be protective of my free time and my work-life balance.

Part of this questionnaire was also figuring out how the work was divided; graciously, Ian still wanted to partner up despite me only being willing to commit part-time. After exchanging questionnaires and doing a bit of housekeeping, we agreed to a partnership, and were off.

Ian was our product owner, and I was the engineer. We both talked to customers, but Ian brought a wealth of product experience that drove the early discussions and decision making. Our early conversations led us to try to help creators in the budding “creator economy”.

The Creator Economy, Wildfire, and Lasso

To start figuring out what to build, Ian and I exchanged ideas. Here’s one of my very early emails sharing some ideas I had:

I keep a running list, as any good entrepreneur does, though this one clearly proves the adage that ideas are a dime a dozen. None of these ideas piqued either of our interest, and we both decided we should maybe start by exploring an audience or niche first, taking ideas from the “audience first” approach that was prevalent in the tech Twitter-sphere at the time.

The creator economy was in its infancy at the time. Big players like Patreon and Substack existed, but it still felt like there was plenty of addressable market. As a creative myself, it felt good to apply my skills to something in this area.

We started speaking to smaller Instagram influencers as well as newsletter authors. We probably had a dozen or so conversations with creators. These conversations turned into ongoing relationships. Their burning question was immediately apparent: how do we make money?

“Brand deals” were the common recommendation, but how does a creator find a brand to work with? The process for doing a campaign was individual to each brand. Some of the creators had at least done deals in the past, and even had progressed to the point where they had built themselves “media kits” to share with brands regarding their audience demographics. We felt like there was something there.

Wildfire

One of our early minimally-viable products was an app we called Wildfire. It used the Twitter API to analyze a Twitter user’s followers. It pulled information like location, bio hashtags, and bio mentions, as well as doing basic topic modeling of their bios to see if there were any ways in which we could segment them. We were initially just doing this for the creators we were speaking to as more of a service offering—an exchange of value for their time (and we genuinely wanted to help them). A few of them found it useful, so we decided to put up a basic landing page and see if anyone would pay for it.

Landing page

Example output for a user

It’s called minimally viable for a reason—this analysis wasn’t comprehensive, and the output was not pretty. But surprisingly, someone paid. I can’t remember the specifics on when we launched this, but I do remember when we got our first Stripe notification. The proverbial “first dollar online”. A rite of passage for internet entrepreneurs.

I was in my car in a Whole Foods parking lot, having just done some grocery shopping, when I heard the “cha-ching” notification. My heart was pounding. I felt a deep existential tug in that moment, like I was stepping off a cliff. In my recollection, I wonder if that tug was the fear from earlier in my journey—of knowing that a stable job might afford more security than intermittent Stripe payments. This simple moment in time felt like a glimpse into all my possible futures—the futures of me building things and making my own way doing it, and of having unlimited agency.

Of course, we memorialized this particular moment.

Then I realized I had to actually fulfill the request. Nothing was automated about this solution; everything was manual. I had to rush home to kick off the job and email this customer their results. So I did. I breathlessly emailed them with a few too many “thank yous” and “please don’t hesitate to reach out”. Then I patiently waited for the waterfall of sales we were about to receive.

We received one or two more sales over the following weeks… but it was a start. That spark turned into conversations about how to take things to the next level. We clearly had something, but not enough of something. In hindsight, we may have moved on too quickly, or may have not spent enough time selling or marketing this idea. The fact that someone was willing to pay $29 $19 (we ended up lowering the price) for a scrapped together MVP was probably more signal than we realized. But our ongoing conversations with our cadre of creators supplied a steady stream of new challenges to tackle.

Lasso

Much of the monetization happening in the creator economy was from user-generated content (which wasn’t a popularized term at the time). These creators needed a way to let brands know what their audience demographics were, so that the brands could work with the creator to build advertisement campaigns, which typically involved the creator creating some specific pieces of content, scheduling their release, and the brand usually paying a flat fee. But again, how do creators find brands to work with?

Our initial iteration of Lasso was a web app that allowed users to login, add various metrics from their demographics, and ultimately end up with a URL, much like the various “link in bio” apps that exist today, but with a focus on metrics. It effectively made them a dynamic media kit. You could get a lasso.so/username URL that would have all of your demographic data, and you could also share a PDF directly with brands. We eventually added some basic integrations with the Instagram and Tiktok APIs to show the users most recent posts, and attempt to gather these metrics automatically. But the workload and context-switching was starting to wear on me.

We continued to talk to creators. We realized there were more gaps when it came to landing brand deals: deficiencies, idiosyncrasies, and small differences between every brand-creator interaction. Complexity grew. We decided we could add more value by being the platform that connected these creators to the brands, automate the creators demographic information, and facilitate the interaction, deal-making, and payment for campaigns.

We were heading for the dreaded “two-sided market”. I say “dreaded” because these types of SaaS products suffer significantly from the cold start problem, only you’ve got two groups of disinterested users who you’re trying to get interested based on the existence of the other group; creators would only want to use Lasso if there were brands to do deals with, and vice versa.

We tried for a few more months to put this together and entice users. Ultimately, I burnt out trying to manage a full-time job with the work of building a startup (not to mention a wedding, buying a new home, and all the other life stuff that usually gets in the way).

After almost a year, I threw in the towel on Lasso and paused on moonlighting as an entrepreneur. An abrupt end to that story, but that’s how these things work sometimes. Ian took the news graciously, and we’ve stayed great friends.

Hindsight

In writing this, I wanted to understand my appetite for entrepreneurship. If I do indeed lack free will, I at least wanted to examine my “cumulative biological and environmental luck, over which [I] had no control” as Sapolsky puts it. I wanted to understand what has led me to this moment, and share that with whoever else might be examining their own motivations, decisions, and journey so far. Obviously, this short bit of writing isn’t everything, but it’s notable to me.

I haven’t made it to Mordor just yet. Being an entrepreneur was and is a dream of mine, and I made an attempt. My first attempt raised a lot of questions: Is entrepreneurship really freedom? What does success look? Is freedom the ultimate form of success? What would have happened if I had quit my job and put my full effort into the work with Ian? Do I really want to be an entrepreneur? Am I going to try again?

Did the fear have anything to do with all this? Is the journey worth more than the destination?

I learned so much, and I enjoyed every minute of it. And I made a lifelong friend along the way. After years of virtually working together, Ian and I met up in person (on my honeymoon of all places) in Lisbon, at a very cool wine bar playing vinyl records.