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I just built my founding team! Five lessons learned.

I've never been more excited about the future of my business. I've been a solo founder for the first few months and have recently partnered up with two cofounders, one core team member, and have a couple other pieces that are falling into place. I decided to share my experience in hopes that some other early-stage founders could find it helpful.

This post ended up being much longer than I anticipated, I guess I'm just really excited. TL;DR: shoot for the stars; be patient; person first - skills second; don't sweat the equity; set rough expectations, get to work, formalize later.

How it happened.

I started by recruiting a CTO after realizing (through a conversation with one of my mentors) that product was a major bottleneck. From the first time I met this guy, I thought he'd be the perfect co-founder/CTO. I reached out to him, we setup a call, had a good chat and he said, "yea mate, I think it would be dope to build a company with you." We went back and forth a couple times about comp - he first said he wanted cash + equity, then said "my bad, expectations were off, happy to work for just equity till we get rolling." I started a bit low (~15%), he told me he was expecting more (25% - 30%), and we both agreed to just get the ball rolling and flush it out down the road, understanding where both of our expectations are.

Next, there was a girl that I had met a few months before in a mastermind at Dojo Bali. As soon as I met her, I said to myself, this girl is amazing - I'd love to work with her one day - not even knowing what her skills were. One day a couple months ago I just decided to send her my thoughts, "I'm not exactly sure what your skills are or what you want to do with your life (she's a senior in college rn), but I just want to let you know that I think you're awesome and I'd love to have you on my team one day." She responded and said, "from the first time I heard about your business in that mastermind, I wanted to work on it - such a cool idea." Turns out she loves writing and studies design - definitely can fit that in. She'll likely come on as an analyst to do content marketing and design (we're matching her with an incredible design mentor).

Lastly, we knew we had to find somebody for marketing. The top person that I had in mind, I didn't think there was much of a chance that she'd go for it. We're pretty good friends, but she just has so much going on, she's pretty well known, and definitely has tons of opportunities coming her way - as well as many of her own projects. I knew she would bring so much to the team because she's one of the smartest people I've ever met, has very high integrity (Naval's top criteria), and was previously in a leadership role at a high-growth company with a similar model. While I thought I'd get turned down on this one, I figured - we're on a role, so might as well keep trying. I just subtly dropped it to her during a co-working session one day, "I'd like to chat with you about doing some marketing for us," and then talked up the promising signals of the business a bit. A few days later, we did yoga together and then got brekky after and talked shop. I told her about the vision of the business and the unique opportunity/culture that we had building a core team of all digital nomads. She resonated with that and agreed to come on board - being transparent about her capacity constraints in the near future. She's going to lead marketing for us - setting strategy and managing the execution.

A couple hours ago, we had our first "exec team meeting." Honestly, it didn't feel real until that moment. It was the first time we came together, talked about the "touchy subjects" like equity, how we'll resolve conflict, etc.; we went through expectations, responsibilities, strengths, weaknesses, risks, our values, and what all of us are expecting out of this. The common thing that grounds our team is that more than anything else, we just want to build something that we're proud of. Something that has a positive impact on the world, sets a good example, delivers immense value to our clients, and allows everyone involved to live great lives. It doesn't have to be a unicorn - we don't have to raise tons of VC or get into YC, we just want to build something great, have fun during the journey, and build lifelong friendships while doing it. If we focus on those things, my belief is that we will all be taken care of financially, that's just the residual result, not the primary.

Five lessons learned.

  1. Shoot for the stars. Many people tend to suffer from imposter syndrome - thinking that we're not good enough. This was absolutely true for me. I had my dream team in mind, but I thought to myself "they have too much going on," "so many opportunties," "my idea isn't good enough," "why would they want to work with me?" As nerve racking as it was (your really putting your ego on the line), I finally worked up the courage to ask.

  2. Be patient. I had some people tell me while I was at the idea stage that I needed to find cofounders. Some siting facts that investors only like to invest in teams, not solo founders. I resisted this because it just didn't feel right. Admittedly, I had one failed attempt to bring a couple team members on a while ago, but that failed because I didn't know enough (afraid to make mistakes, I low balled offers to two talented people - a couple thousand cash and 5% - 10% equity). After that failed, I ended up building the MVP by myself with no-code, launching it, getting some customers, learning soooo much, and proving my ability to get sh*t done. The learning from the initial beta launch made me so much more capable when it came to recruiting co-founders. I now had a better sense of what the business was and what we needed to make it successful. This is much more compelling than having an idea on paper.

  3. Person first - skills second. The way that I thought about it was, if I wasn't building a company, would I want to be friends with this person for the next ten years. I believe this will allow us to build a great culture, where people love to work and engage with colleagues. We'll all likely need to be doing a bit of everything - learning new skills and markets, so the most important thing to me is just having great people that are smart, humble, have high integrity, and common values.

  4. Don't sweat the equity. When I first started this company, I was so worried about giving away too much equity. Thinking each percentage could be a million dollars. If that ends up being the case, we're all going to be taken care of, so I'm not too worried about it. At one point I even had the realization that I could either (a) raise money for much less equity and hire people with cash comp or (b) not raise any money and give away a LOT more equity. I chose to go with B because that means that our founding team is completely bought into the mission of the business. If we ever hit a rough patch, the chances that people will stick with it are much higher, rather than seeing it as an opportunity for a paycheck on day one.

  5. Set rough expectations, get to work, formalize later. I came across this idea in a recent podcast or blog (can't remember exactly) and it was very helpful. It's really hard to assign equity on day one working with people. Instead, we talked about a high level range 15% - 30% and said we'd revisit in a few months. This allows us to learn more and see how everyone is contributing before making the formal decision. We'll back-date vesting periods to start dates, but this just allows us to get started without wasting too much time on less educated decisions.

I'm incredibly excited about the official launch of MentorPass.co in a couple months. So far, we've just been in a beta solely focused on learning from the market, finding our fit, and recruiting the best cross-functional team of startup mentors. Building the MVP myself was a great learning experience, but I'm really excited to be able to step back into my zone of genius and have a few talented team mates that will be able to thrive in theirs. New brand, product, and offering coming soon.

on February 25, 2020
  1. 4

    Kenny, gonna be honest - it is never a good idea to kick the can down the road regarding cash/equity conversations... (common first time founder mistake)

    Also - think about opportunity cost for your team around you. Sure they’ll help at first, but if you aren't paying them, equity only goes so far.

    Sincerely, skeptical cheerleader

  2. 3

    Love the sentiment but horribly naive. Report back in a year. Most things, especially financials don't "just work themselves out". People are super nice until it gets to splitting up the pie (when there is nothing, and then when there is something). Still, I wish you well.

    1. 1

      Well said. Only thing that matters in this type of business is lifetime value of a customer and cost to attract a customer

  3. 1

    Congrats! I look forward to hearing more from you and MentorPass! Keep it up!