I’ve been fortunate to work with exceptional founders. Being an active angel investor one of my roles is to build a partnership with my founders and be the first call when they need me. These are some of my views on how I approach building enduring companies and life.
Life goes by quickly, so it’s important to really pick partners that you share values with.
Pick partners — whether it’s co-founders, early employees, angel investors, VCs, or executives - who share the same long-term goals as you; they should really believe in your vision and have the same value sets. You want someone that you can partner with for a long time because life is too short to be tied together with people you aren’t aligned with — or that you don’t like to spend time with. There’s plenty of great talent out there so pick for the long term partnerships.
I’ve been a VC previously and also had some great success as an angel investor. I’ve also been lucky to have been at several startups as a co-founder — one that had a lot of growth.
Alongside that, I also started a non-profit that has been super successful as well and had a lot of growth by taking a venture backed approach on how we grow.
I understand that founders need sounding boards, and some VCs will act like a parent, but I prefer to act like a partner.
The founder journey is very lonely or at times can be very lonely. In the good times there’s plenty of people to go celebrate the wins with. I want to be there to help celebrate the wins also, but I absolutely want to be there when the founder needs someone to talk to and be their first call to make.
Having everyone aligned on a clear vision, mission, and values from day one is very helpful.
Everyone needs to understand your long-term goals, so you are all on the same page. Sometimes you have to deal with a rockstar that doesn’t align on your core values and they can be a cancer to your company. It’s important to deal with them early to avoid issues in the future.
Over time, as organizations get bigger, culture is going to change a little bit because it’s hard to find the people with the exact culture fit. That being said, it’s important to try and bring people in with the right values and the right vision because these behaviors are critical to your growth and culture.
When I meet founders, I like to hear and understand their origin story.
The little details matter, and I care about all of them. I want to know why they started the company, what the inspiration behind it was, and what their personal motivations are. It’s important for founders to be very aligned with the mission.
It’s also important for founders to have their skin in the game. It doesn’t have to be cash, but it could be that they quit a very high paying job and learned how to code through a boot camp over a year. Putting in time and energy not only shows conviction but also builds it over time.
Early-stage investing is a tough game — professional investors know they’re going to lose some money. It’s not all going to be successes, so when founders have friends and family involved at an early stage, it shows a level of conviction that’s hard to meet. That makes a big difference.
Conviction tends to show in founders because they are constantly climbing up a mountain, so they have to be very resilient and persistent. People show early signs of these traits, and it’s important to look for them. I try to understand people’s backgrounds because that often builds character and makes them who they are today.
The founders’ journey is a special one, and it’s also unique. It takes someone with special character traits to be a founder. What’s unspoken is that it can be very isolating. You’re the only one with a lot of pressure on you, from every angle: it’s your executive team, your employees, your customers, your shareholders, and your board. To add to the pressure, oftentimes, many founders are doing it for the first time.
In this respect, co-founding teams are usually better because you can lean on your co-founders when times get tough. Hopefully, they are two or three people that compliment each other and bring something new to the table.
In the same light, when I’ve been a founder, I found it productive to lean on mentors and advisers — whether they’re angel investors or VCs. Effectively, people that are equity incentivized. People who have done it before and have walked in your shoes can be very helpful in helping you do it-- especially in the early stages.
Founders need a sounding board because they’re dealing with so much at once, and I like to be one.
Being a founder is also exciting because most great founders have risk appetite, love challenges, and have resilience and determination — so it can be an exciting journey because life is about experiences.
Along the journey remember to enjoy the moments. So many startup founders are so focused on the company they don’t enjoy or celebrate the little wins. You need to celebrate the little wins so that you can endure because the startup journey is not short.
Founders can have an edge that can be a unique insight into the industry or space. It could also be a personal passion or a personal connection to why they are trying to solve an issue in the market.
Sometimes the reason founders start is that they have an intrinsic connection to the problem because that problem affected them personally. Those solutions that founders solve for themselves can sometimes be a product or service other people want.
Some of the online conversation may make you think insight is the only way to start, but passion and drive can be an edge in themselves.
One of the things early founders under-invest in is a head of people or an HR partner. When you’re at 20 to 25 people and growing your headcount 50% to 100% YOY, you most likely need it. Most founders won’t bring them in until over 50 or 60 people.
Talent is everything with a startup, so being able to recruit like-minded, exceptional talent, needs to be a key focus at the start because it only becomes harder as you grow. An HR leader jointly taking the lead on talent with the founder can be very helpful.
When you get past 30 to 40 people, it’s hard for a founder to interview every single person. They become a bottleneck. They have to let their co-founders or executive team or early management leaders hire their people, and that can be a very tough transition for a founder to let go of. There’s a very fine line there.
My other bias towards building organizations earlier rather than later is hiring a great executive coach — it can be super useful for a first time founder.
Oftentimes, an executive coach is an unbiased, non-tech, non-startup leader who discusses leadership — or gets the founder professionally trained. They lay the foundation to let the founder work through a coaching type of atmosphere and have no equity or ties to the board. Almost every great founder I know will have an executive coach at some point in time for themselves. This is not really spoken about publicly, but it is very common.
I’ve always been involved in sports as a little kid because it’s a great outlet to stay active. However, it’s also just a lot of fun and brings a lot of learning lessons. I played soccer in college and basketball and soccer in high school.
These were all team sports. I liked practicing with a group of people with a common mission and being competitive on game day — and quite frankly, even in practices. After college, I continued to stay active and got involved with running and triathlons.
There’s also a lot of learning lessons that helped make me who I am. Whether it’s playing well in a team, strategizing on how to beat an opponent, or having grit by overcoming an injury to finish a game.
The lessons I have learned from these experiences translate into who I am today because I like to win. I like to play in a competitive atmosphere with other people, and I have fun doing it.
One Goal is an education non-profit I co-founded, whose mission is for every child in the U.S. to have access to a 4-year college degree. We started 16 years ago in 2004, as a volunteer organization with two classes of 20 kids. All of those determined students went on to attend college. It was started in Chicago, and 90% - 95% were first-timers — as in their parents didn’t go to college.
In a small sample size, all of them got there and it was because we found a great teacher who wanted to help them. Today we have 13,500 kids, of which over 80% get into college and another 20% are persistent — and 95% of them are first timers.
In life, success is great, but you have to give back. I’ve been involved as a volunteer for a long time, but I’m thrilled that to an extent I can give back to a community that has given me so much.
For all young people in the beginning of their careers looking for their next step, it’s very helpful to find a mentor.
Find an adviser or someone that you can learn from because learning is probably the most important thing early on.If you find the right person, whether it’s a boss at a company or whether it’s someone outside the company, you can just grab on to their coattails. If they’re a fast-moving train, you can just grab on and you’ll go along with it — but the bigger thing is you’ll just learn a lot earlier in your career.