Collection of Lessons from a Startup Founder

The most formative moments of my life have been those in which I’ve been thrown into the deep end, forced to stay afloat. When life is on the edge and you’re desperately trying to balance yourself, every decision matters. It needs to be calculated yet visceral. In fact, several factors are at play influencing most of our decisions. There’s often a time constraint, a cognitive constraint, an environmental influence, a subjective propensity to risk, and finally almost always a budget constraint. Since embarking on this entrepreneurial journey of self-discovery six months ago, I’ve made decisions that proved to be both good and bad and have learnt several immutable lessons that I’d love to share.

**A disclaimer is that these are my personal takeaways, not advice I’m trying to give.**

Lesson 1: Emotional decision-making is blindsiding.

When my co-founder Aris and I first set out on our journey, we had no fucking clue what we were doing. Every day, we’d plan our action items and set relatively realistic goals. Some days we achieved them, but most days we fell short. Why? Because we’d spend at least two hours every day scenario planning. We’d let our incidental emotions and personal biases influence our decisions, which ended up destroying our productivity when things didn’t go our way. Being attached to our ideas really harmed us. Every time something didn’t go as planned, we took it personally and felt like the world was falling apart. A few months in, the emotional rollercoaster we were on definitely took a toll on our mental health. We gradually realized the need to stop overthinking and start performing tasks with a limited emotional attachment, which has since helped us prevent many existential crises.

Here’s a graph that we made outlining our fluctuating daily emotional trajectories.

Lesson 2: Altruistic investors are non-existent.

When we first started getting traction on Mobility, we were pleasantly surprised to see a bunch of investors cold-emailing us asking for intro calls. Given our limited budget and the fact that we were nowhere close to making revenue, we knew that we’d need a financing round soon. However, it was clear that at the time and still now, we weren’t ready to raise. More important priorities included building our MVP and testing for product-market fit. It’d be a waste to raise a round, dilute ourselves, and not know how to spend the money. Even though we had a vision, that alone wasn’t enough. Given the abundance of capital in the market, investors pressured us to begin the conversation so that they’d get a good deal at a lower valuation early on. Most of them have their own interests in mind, not that of founders. It took us a lot of time and energy to realize that.

Lesson 3: The burden of loneliness is heavy. Find a community outside of your team.

When your work blends into your life, it becomes hard to separate the two. Since we worked from home most days, my co-founder and I spoke to almost nobody outside of ourselves and people over Zoom. Oftentimes, we forgot about the need to interact with others. Although we did have a dedicated space at the Pennovation Center, it was still difficult for us to find a like-minded community that we wanted to be a part of. Through this experience, we learnt two vital things: the importance of developing real-world human connections and the need to consistently nurture these newly formed connections. As a result, last month we made the decision to move to New York City, and a huge deciding factor was to join the thriving startup ecosystem there. In fact, starting February, we’re especially excited to join Launch House, a community of entrepreneurs living and working together.

Lesson 4: There’s nothing that can’t be learned.

We made a mistake early on by hiring a third-party developer from Upwork to build our initial website. We spent $5k building something that we easily could have built ourselves. Our reasoning was that we didn’t want to waste time building a website over doing more important things such as speaking to customers. However, it quickly became apparent that it took longer to communicate our vision to an overseas developer than to do it ourselves. As a founder, our job is to learn and be as scrappy as possible — what else are we going to spend our time doing? As a result, my co-founder and I built our second website and functional “minimal viable test” by ourselves in a week, saving both time and a boatload of money. YouTube videos are really a life saver. Moving forward, the goal is to become experts on the niche segment of our industry we’re working in. Nobody in the world should know more about the D2C home healthcare market than us.

Lesson 5: Starting a company is just a series of experiments. Don’t be afraid to pivot.

In college, I spent a lot of my time working in a DNA repair lab experimenting on BRCA-mutated cell lines. Most of these experiments led to disproving an initial hypothesis. Even when the results seemed statistically significant, we were required to perform multiple replicates to prove that the prior scientific findings occurred and were not false positives. I didn’t realize that this scientific method could be applied to other aspects of my life, such as building a company. I’ve come to learn that going about testing your initial ideas as a founder is very similar to writing a scientific paper. It’s a series of experiments that need to be performed concurrently. If one experiment doesn’t work out, we record it and move on to another. We quickly realized through customer interviews that telehealth-only solutions weren’t going to outperform in-person visits, leading us to integrate a hybrid approach of delivering care to our model. The faster the rate at which you experiment new ideas, the quicker you’ll achieve product-market fit.

Lesson 6: Find product-market fit in the least expensive way possible.

The road to achieving PMF is long and arduous, something we’re still personally journeying on. Given the limited amount of resources available to us (and to any other early-stage company), we realized the need to optimize both our product development plan and customer acquisition strategy in order to spend the least amount of money to achieve PMF. Unfortunately, this epiphany came a little too late, after we had spent upwards of $20k on customer acquisition through paid media efforts. We easily could have gotten over this initial customer acquisition inertia through strategic partnerships with health providers. Since we were so focused on proving we could directly market to consumers (i.e. patients), we didn’t think of other creative avenues to initially acquire a loyal patient base through B2B acquisition channels. The bane of any D2C healthcare company’s existence is finding the perfect go-to-market strategy. The key we realized is to figure this out in the most cost-effective way possible. Doing so would allow us to test way more experiments (see Lesson 5). We took a couple expensive turns but think we’re finally on the right track, at least for now.

Lesson 7: Having a sense of direction supersedes working hard.

We get pulled in a million different directions every single day, and it’s been very easy to get distracted on what tasks to focus on, especially when we don’t even know where we’re headed. A skill we’ve tried to learn is to confidently outline our priorities and more easily say no to the things that don’t really matter. Our biggest flaw as a team is that both my co-founder and I want to do everything. It’s very hard for both of us to turn opportunities down, even when these opportunities turn into opportunity costs. Today, we make sure that the work we do every day is either helping us learn about a specific topic or helping us build a better solution for our customers. If it doesn’t fall in either one or both of those categories, we table the task. The example my dad always brings up reflects what I think this lesson means flawlessly:

You’re located in Philadelphia and your goal is to travel to New York City. No matter how fast you drive, if you’re traveling in the direction of Washington DC, you’re never going to get to where you want to be.

Lesson 8: Simply put, my job is a salesman.

I never thought I’d grow up to be a salesman, but this is my job as a founder. I learnt that I have to sell not only my idea but also myself to literally everyone with whom I interact on a daily basis. Customers, investors, partners, potential early-stage employees, friends. I’ve become a living Shark Tank episode, and the line between the real and the imaginary is starting to look very blurry. In October, I spent almost three straight weeks in Rittenhouse Square (a park in Philadelphia) talking to random strangers asking them if they wanted free health visits. A lot of rejections later, I can safely say that I have a newfound appreciation for spam callers trying to sell me their auto insurance. It’s part of the process, and both my co-founder and I have come to embrace it.

Lesson 9: Stop brainstorming. Just fucking do it.

We all have great ideas. I probably generate more than 10 new ideas that I think are brilliant on a daily basis — this is obviously subjective because most people think my ideas are ridiculous. An idea doesn’t mean shit if it isn’t going to be tested. Think of it as a large piece of rock sitting on top of a mountain, filled with potential energy. Sure it’ll require some activation energy to get that piece of rock rolling down but once momentum kicks in, there won’t be much to do after that. All of that potential energy will have just been converted into work (aka value creation). The idea in your head is that piece of rock. Don’t let it just stay there accumulating dust.




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Yiwen Li

Yiwen Li

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