How did Trust & Will get started?
Trust & Will was an idea that came to me out of my personal experience. I am a serial entrepreneur -- this is my third startup -- and I was thinking about my next idea while also planning to get married. As my then-fiance and I started making plans for the future, I wasn’t sure where to start with estate planning. That threw me off. I started looking to see if there were any products or services to help people with this process, and I couldn’t find anything on the market, so I didn’t take any immediate action.
I then connected with my friend Daniel, now co-founder. It’s a crazy coincidence -- he actually met to pitch me on the future of digital assets, and estate planning became the core focus of the conversation. We put our heads together, did 2 months of research and exploration, signed on Brian (our third co-founder), and planned out what this might look like. Also, by some magic, the domain trustandwill.com was available. I’m still not sure how, but this was a sign for us to go for it, so we bought the domain, entered a pitch contest, and made it happen.
You mentioned this is your third startup, what happened with your other two companies?
Trust & Will is my third startup, so I have some experience and practice with failure.
My first company, which I worked on around 2012/2013, was what I call my “practice run.” I was right out of college and had no idea what the hell I was doing. It was at the time when Instagram and Snapchat came to market. My app — called Niche — was similar to these, but instead it would unlock content based on geography, so users would only see and share content if they were in the same space. The app never solved a core problem, and the competitive landscape had too many well funded players, so we ultimately shut it down.
After Niche failed, I worked at Seasons 52, a fine dining restaurant. I was immediately blown away by how hard it was to get a job in the industry and by how offline the hospitality job market was. So I launched Industry as a LinkedIn for the restaurant and hospitality industry. That company actually took off and helped me gain experience as a founder and CEO of a business. We went on to raise millions of dollars, grow our team to 24+ people, and more. The company is still operating today and being run by my former co-founder.
What have you learned as a founder?
The #1 lesson I’ve learned is to work with really good people. Your co-founders are your family. In most cases, you are going to see them more often than your family at home.
You want to surround yourself with people who are personally aligned with your values. This is more important than any other business background.
In fact, I work on a legal app, but I’m not an attorney and neither are my founders. What bonds us are our values. These are key.
The next thing I’ve learned is to extend that approach to your team and to pull from your immediate network as you build your team. This lets you have a foundation early on. For example, I have two senior engineers at Trust & Will who I worked with on other ventures. I can work with them at almost a nonverbal level -- we just work well together.
What’s it like working with two other co-founders? How did you find them?
I love my co-founders. In the early days of the industry, I was a bit of a pitch competition guy; I kept showing up to events and pitching my ideas. There was one competition in San Diego that we won in 2014, and Daniel (my co-founder) was at that time volunteering at the event. He came up to me after my pitch and we just hit it off from the start. Daniel and I made an effort to meet up every couple of months to talk tech, and our friendship has only grown stronger over time.
Brian, my other co-founder, was leading the design team at the same agency as Daniel. We made an effort to keep in touch as well over the years, and when Daniel suggested we pull Brian into the co-founding team for Trust & Will, I knew he would be a terrific addition.
You say you did a lot of pitch competitions. What’s your advice for people entering a contest?
Practice in front of smartphone, record it, and watch it. See how non-verbals like your projection or tone work. Make sure you scan the room and include intentional pauses. For any pitch, practicing and watching yourself is the best thing to do.
What is the most important skill you’ve gained having founded three startups?
Getting to know investors and the startup community. It’s all about relationships, and I’ve been very lucky to get to know investors and maintain those relationships over the years.
That’s another reason why I’m so excited about Republic. My hope is not just to raise money, but how we can get more individual investors as excited and enthusiastic about the vision for the company as I am as a founder. We plan to send them regular investor updates, LinkedIn requests, and even put them to work with some soft asks (like helping connect us to people in their networks). Engaging this new base and building these relationships is something I’m really excited to test out.
When things go south, what keeps you going?
I take a step back. Every morning I do a gratitude exercise on the Calm app. I express in my own head what I am grateful for, such as my family, wife, friends, the fact that I live in San Diego. I reflect on the fact that life is actually pretty good. I then try to take that energy with me into the office.
As a founder, when you walk in the doors of a startup, you can go in thinking it will be a great day and it turns out to be a not-so-great day. When it gets really hard, I’ll do a breathing exercise and focus on what I need to get done that day to make me feel accomplished. It can also do the reverse; you can come to work in a bad mood and it can turn out to be an amazing day. It’s the nature of the business and I remind myself to appreciate this journey.
What were the 3 hardest things you’ve done as you’ve launched your business?
Overcoming objections. I love my product, but we had a lot of initial objection from an older demographic. Many people were telling us that young people are not going to use our product, so we had to come prepared with data to show them that they are wrong.
The competitive landscape. Every founder has to worry about competition and a crowded market. In our industry, LegalZoom is really the only legacy online legal player in the U.S. This is something they’ve been doing for over 20 years. We saw them as a pseudo-competitor, so we went to meet with John Suh, their CEO. On a personal note, he is a super nice guy — he exemplifies everything you want to be as a leader and a CEO. He had a pretty honest conversation with us and shared some key differences in their target audiences which equipped us with the materials we needed to go back to investors and help overcome objections.
Doubt. The thinking whether you can you actually do it with limited capital and a small team. What really helped us overcome this was participating in the Techstars accelerator. There, we found a lot of helpers — from angel investors advising on product, to advice on marketing and our business model. This was very rewarding early on in the company.
What is your superpower?
I can be friends with just about anybody. I will accept anyone into my network with no judgement or perception. I really try to make a connection with people when I meet them in person, and I try to maintain those relationships, even in a light way.
What’s your kryptonite?
I get too excited about everything sometimes. I like to be a yes man. Saying no is hard because I love connecting with people, but I have to be realistic with the promise I made to myself as a founder, and to our team, investors, and customers. We have to work hard everyday and if I say yes to everything, that takes energy away from that.
What does a typical day look like for you?
My alarm goes off around 5:35 am. This is my cue to hit snooze for 10 minutes. I then go to the gym for about an hour, meditate with the Calm app, and get in to office by 8 am. I check emails for about 30 minutes and prioritize what I need to get done for the day. I then prep for the day’s meetings and figure out if others might be more involved in that prep (for example, if we need to create a pitch deck, product demo, follow up on next steps, etc). No matter what I make sure either I’m prepared or my co-founders are prepared. We also have a team standing meeting at 10 am every day — that’s a big one.
Do you have any unusual routines or habits?
I’m always the first one in the office. I also think my coworkers would say that I’m guilty of getting excited over anything — from a big partnership to a great customer review. I’m a forever optimist.
Do you have any other hobbies/things you like to do? What do you geek out about?
I love spending time with my wife. I try to cook dinner with her every night.
I also serve on the alumni board of San Diego State University as the VP or Partnerships. I’m trying to get more tech businesses involved and helping with young alumni board development. I think this goes back to my love of connecting with people; I like to help people out.
What’s something you wish you knew more about?
Technical knowledge. I can communicate confidently with my engineers in a general sense, but if I ever had a transition time or time to do a coding bootcamp, I would love to grow that base knowledge and be able to have higher level conversations with the tech team. It would make me feel more confident.
What’s the one (ok, two) books you recommend everyone read?
Blitzscaling by Reid Hoffman and Chris Yeh. I think this should be in the founders handbook.
Venture Deals by Brad Feld. This is the most important book for any founder that is going to raise capital. It’s essential.
Who is someone that has changed your life?
I’ve had one mentor who has had a particular influence on my life and that’s John Buffini. He’s a life coach and mentor that works with a lot of founders and executives. I actually met John by bumping into him at the gym. We started talking and he invited me over for a coaching session. I thought he was just trying to sell me on something, but within 10 minutes he identified my greatest weaknesses (which freaked me out) and captured my core competencies. Over the past four years, John and I have developed a great personal friendship and professional relationship. He always gives a strong pulse check on my progress and evolution as an entrepreneur. It’s funny; he’s a random person I met at the gym that has totally changed my life.
Any advice you’d give aspiring founders?
Google your damn idea! I get pitched ideas all the time and it’s obvious that no one has Googled it to see if it already exists.
Also, if you see an opportunity, think about whether you are riding a trend or solving a core problem. You can be successful in both, but I think there's a stronger place for the latter.
Lastly, customer validation matters so much. I didn’t do this at my first startup. Start with 25-50 people. Send a survey. Get the validation from potential customers to help with your research.
If you could give yourself one piece of advice 5 years ago, what would it be?
Find really strong mentors. When I first graduated college, I had the confidence that I could do it on my own. That was a mistake. Whether you have help from co-founders or you can tap into a network of entrepreneurs that are just a bit ahead of you, you want to find people who you can ask those tough questions and help guide you through the early stage challenges that people often don’t talk about.