8 Lessons I Learnt From Founding my First Tech StartUp

Early on, many of my VC and serial entrepreneur friends urged me not to indulge potential team members with equity arrangements until they had proven that they could deliver on what I would be hiring them for. Here was where I made my first mistake- In my paranoia of bringing people on board too quickly, I avoided having conversations regarding incentives entirely, which demotivated the engineers I was in conversation with. (Lesson 1: Always have conversations about compensation as early as possible to gage commitment from your prospective hires.) At the time, I was bootstrapping on a shoestring budget, while attending UW full-time, and funneling all of the fees I earned from consulting for a couple of startups in the area into Evalise. Therefore, most teammates were on part-time consulting agreements; Most of the engineers were under verbal agreements that we would bring them on part-time at first, then full-time once we got funded.

I’d engaged several hardware accelerators and funds in the silicon valley and scheduled pitch meetings with them. To prepare, we were going to build our first fully functioning prototype. We had around a month and a half to pull the pieces together, and I’d put together a calendar and basic PRD (product requirements document) to get the ball rolling. Up until this point, the engineering team and I had been focused on fleshing out the concept from head to toe; This was my test to see who would take the initiative on creating our first physical prototype for the insert, our flagship product.

One by one, every single one of my prospective engineers opted out of creating the product… And it was entirely my fault. Product development was no longer focused on having fun in conceptualizing, and I was creating anxiety by being hyper-focused on getting to-do’s checked off the list. Had I been more clear in my communications and incentivised the team appropriately, the right people may have stayed on board. This is when I learned that there is a huge difference between someone who is interested, and someone who is committed. (Lesson 2: Figure out as quickly as possible if someone is 100% onboard or not. If s/he is on the fence or looking for a reason not to move forward, move on.)

Fast forward to the last ball being dropped- I was left with a week and a half until I flew down to San Francisco, with no engineering talent, no prototype, and my mother’s guest room full of every trinket from Vetco. (I moved back into my parent’s place to save up for the company expenses.) At this point the question became, ‘what to do?’ To which, without hesitation, I answered myself, “there’s no f*cking way I’m losing face at my meetings in the valley. I’ll do anything and everything in my power to make this prototype myself; And if it doesn’t work, at least I’ll go down swinging.” So I started going through my list of contacts, calling every single person who might be able to help me make the prototype. Luckily, a friend of mine who had just sold his fourth startup as a CTO and founder decided to help me. For that week and a half, I worked around 20 hours a day, making several trips back and forth to Vetco and his office.

A week and a half later, we had our first fully functioning prototype- Conductive thread sticking out of odd corners in different colors, excess glue extending past the magnets, and a huge box for the Raspberry Pi adding an unnatural bulk to the middle. It wasn’t pretty, but here it was, it worked, and with the help of my friend, I, a person who had never written a line of code in my life, had built it. I admired it as a mother would look at her newborn… In complete awe. 

This was a key turning point for me in many ways- I learned that if there is something I truly want, I can make it happen 99% of the time; provided that logic permits, of course. I also discovered how little of my own capacity I was really engaging most of the time. Since then, my primary goal has become to push myself to the limit of my own capabilities and reach deeper to see what I can really accomplish. (Lesson 3: You are more capable than you think. Don’t give up until every cell in your body senses that there’s nothing you can do to shorten the odds against you.)

Without a moment to breathe, off I went to San Francisco. My meetings all went very well- I got asked to return for follow on meetings from nearly all of my meetings, with the main message being that I needed a technical co-founder in order to further the conversations. I returned entirely disillusioned with my hiring processes. This time, I told myself, I was going to find someone who was scrappy, hands-on, and ready to dive in to make the product.

While I searched for a CTO, I had a fellow fashion tech founder help me source a manufacturer in Vietnam. A CTO/serial entrepreneur friend told me that I needed to make CAD drawings to effectively communicate what I wanted for our samples if I planned on taking the designs overseas. I therefore hired an (expensive!) intern from Stanford to make our CAD sketches for us. It took at least three times longer than I thought it would, and I was running dangerously low in cash at that point; But at last, we had the diagrams. I created several descriptions and summaries to help them explain in depth, along with hand-drawn sketches, and spoke to my fashion tech founder friend about what I was looking for. He agreed to get samples for me from Vietnam on his way over. When he came back, I was ecstatic to see the samples- My excitement sank and turned into a sinking feeling in my gut as I saw the samples, which looked nothing like what I’d asked for and were practically useless. Turns out, the guys in Vietnam had zero clue how to read CAD drawings. That sinking feeling turned into a flutter in my stomach as I further learnt that he had agreed to a price that was more than twice the initial amount we’d decided on. The irony of this instance, is that I, like many first time hardware founders before me, had heard the horror stories related to production and sought avidly to avoid being the subject of one. And yet, here I was, living in one. (Lesson 4: Be VERY clear with whoever is managing your supply chain about exactly what you’re looking for and set a budget printed and signed.)

A little while after this disaster, I found my second CTO- He had left his post as a former C-suite executive of the air force, and was eager to get back into hacking. While our interactions furthered, Evalise got scouted for the Intel Makers competition. After making it through the first few rounds of interviews, we were getting ready to plan our trip to Santa Clara for filming. I had a gut feeling that I would be getting a call from my new CTO that he couldn’t make it. (Lesson 5: Don’t ever let your desired outcome cloud your judgement of what your gut and logic tells you it could actually turn out to be.) I had decided that if that was the case, that I would decide to close up shop. Not only had I run out of money, but I also didn’t have any technical expertise of my own to combat our product development needs in a long-term and sustainable way.  

Sure enough, exactly a week after having that conversation with my mother, I got the call from him. He had found some other work that could really pay- He wouldn’t be making it to Santa Clara. I knew at that point that it was pointless to convince him; He had made up his mind, and now, so had I. It was time to dissolve the company- I felt it. (Lesson 6: Know when to move on. That intuition of yours comes in handy here, too.)

Had I wanted to, I could’ve raised money for about a year prior to closing shop- We had a bit of interest from a few angels in the area. But I knew I would be doing it under a compromising situation in which I hadn’t fully gotten everything fleshed out. We weren’t ‘there’ yet- I wanted to fully vet product market fit before bringing investors on board. Taking investor dollars is no joke! I’m glad I didn’t pursue fundraising, and  chose, instead, to dissolve the company. There were too many loose pieces in the mix, I was not in an environment that was conducive to the objectives of the company; I would’ve lost the money and made a bigger fool out of both myself and anyone else involved. Thankfully, this was a lesson I didn’t learn, but it should be mentioned nevertheless: (Lesson 7: Never take investor money unless you are managing 100% of the risk you can manage effectively and are on firm footing- If something feels like it’s not quite ‘there’ yet, work on it before you engage investors if you can.)

After dissolving the company, I took several months to digest- This is a valuable time to understand and learn, but the lens through which you look at things is equally important- While it’s important not to bottle your feelings, tainting each experience as a ‘failure’ is counter-productive. If you’re in the startup game for the long haul, you know what you signed up for and it’s important to be invested in your present in order to build an incredible future. (Lesson 8: If you focus too much on your past failures, you’ll never gage value out of your present.)

I’m worlds away from where I was when I first started Evalise- I’ve not only grown tremendously as a person, but I’ve also refined my process and skills and have a far wider breadth of knowledge of how to build a startup; Which can only continue to grow. In every sense, it was an incredibly worthwhile journey.