From MBA to Entrepreneur Part 2: John Koelliker, Leland

John Koelliker always knew he wanted to start his own business. From a young age, his entrepreneurial spirit shone. Whether it was starting a baseball company that sold gear in Nordstrom and J Crew or his side hobby of helping young students get into MBA programs of their dreams, he was always working on something new.

Because of this, it was no surprise when John, and his co-founder Cameron Lehman, started Leland, a coaching marketplace that helps ambitious people reach their goals — starting with MBAs. John leveraged his expertise in marketplaces from his time as a Product Manager at LinkedIn, Uber and Curated, as well as his knowledge of the MBA admissions process to solve a significant issue that he knew very well.

“[Through my consulting] I think I got a lot of insight into the pain points that applicants feel. The demand side [students] in this market want expertise from someone and don’t know how to find it, how to afford it, or how to trust it,” John said. “As I dug into the supply side [coaches], I realized that these admissions consulting firms are charging $10,000 or $15,000 because the firm itself is taking 50–80%.

He quickly realized that by making the process more efficient, he could save candidates more money while helping them achieve their goals, and simultaneously put more money in the pockets of coaches who were frustrated with their returns. Leland made it easy to search for the right coach, ensure they were within a student’s budget and facilitate the interaction. Coaches didn’t need to set up a marketing funnel or build a website — they only needed to do what they do best: coach.

They’ve already seen tremendous success since its foundation in January. The company recently officially launched in July and closed their pre-seed round of $1.1M led by Contrary Capital and Peterson Ventures. While the company continues to grow, their vision is much larger. “The idea was always to start with MBA’s because it’s a space we understand well to get off the ground quickly. If we decide to expand to other verticals in the future, we’ll have a strong supply base to build on.”

I sat down with John to hear about his path to entrepreneurship, his learnings as a founder, and his time management as a student.

As a non-technical founder, how did you build Leland? Is there any advice you would give to other non-technical founders?

We had a few options. One of which was to build the product using no code tools like Bubble and other similar programs. However, those don’t scale super well and we wanted to build on top of ours so we wanted to avoid those if we could. Another option was paying for a contractor but the options domestically are expensive and those overseas aren’t always as consistently good. We ended up using a few engineers from major tech companies on a part-time basis to build our MVP. This allowed us to build in a much more scalable way than writing a bunch of code that kind of gets Frankenstein-ed together. it’s a lot easier to recruit people to work on something part time right now than it is to do something full time, especially with remote work.

How did you go about finding a co-founder?

I think one of the interesting things is that Cam and I are not lifelong best friends, which I think is actually valuable in some ways because we built much of our relationship around this company. Obviously we care about each other personally, but also it doesn’t feel like we are wrapping up all these other external factors along with our relationship that we have to be careful about. We’re going to make this thing work and it’s a very Leland focused relationship. That doesn’t necessarily mean only a business relationship — we still have a lot of personal conversations but I think that’s been really helpful.

I think just trying to be transparent and giving each other open feedback often is crucial so we’re always in sync. I don’t know if there’s any recipe, but I would recommend that the right person I think is someone who isn’t a quitter, is humble enough to admit when they’re wrong, and cares about the company. If you pick a family member or friend, I think it is important though to know that your relationship is never going to be the same. It doesn’t mean it’ll be a bad relationship, but businesses are stressful.

Many companies are now moving into a distributed work environment. How have you thought about this challenge as you build out Leland?

We are trying to hire most full-time employees in either the Bay Area or Utah. Currently, everyone is distributed as we don’t have an office but everyone is in those two geographic regions, which is important because then we can still get together if we need to. I think we’re still kind of torn on a fully remote employee for full time hiring — if we found the absolute perfect person I think we’d be open to it. However, I think the goal would be some sort of hybrid model where we’d be split between the bay and Utah and we’d go to the office a few days a week.

I just think there’s so much value in being together that you lose by being remote so I don’t know. I think we’re still figuring that out but I think because we’ve at least tried to draw the line around mostly being in Utah and the Bay Area so that’s been helpful.

How has Stanford and GSB been supportive in building your company?

Stanford has several amazing resources for entrepreneurs. The student community is unbelievably helpful and supportive — we are basically one classmate away from an intro to any top VC fund or whatever person that we need to reach. That’s been really valuable, so it feels like we have this army of supporters.

Also, a lot of coaches on Leland are some of my classmates. We obviously have some super experienced coaches, but we also have some that are current students or recent alumni that are a little bit more affordable. Some of my classmates have made money coaching on Leland and it’s fun to be able to support them while allowing them to help the next generation of applicants.

With so much going on in your life, how do you prioritize your time?

It’s super hard. I am a dad, I have two kids and I’m married. I also have the startup and school and I’m not going to stop doing any of those things so it just becomes an exercise in fitting it all together. I think it’s setting up a structure that allows me to block my calendar and go deep in certain areas. I think it’s just about prioritizing and getting my stuff done for school, but really Leland has been the top priority so anytime I have downtime I’ve been focused on Leland.

Starting a company is often a lonely journey, what does your support system look like?

I’m still figuring that out. My wife’s been super supportive and helpful and my kids are really good at reminding me what matters without them even trying to. When I’m really stressed about something, I come downstairs and my son just wants to play so I pretty quickly realized that the stuff that we’re building is important but fortunately it’s not life or death. I just want to do my best and make sure the company is growing but I think kids in some ways forces a perspective and forces you to turn off at times which is healthy.

Also, having a community of other founders is so helpful. I have a couple of friends that are further along than me and I ask them questions all the time. They’ve just been amazing mentors and support systems for me. There are small things that you just don’t even think about until you’re starting a company like how much of my employees health insurance should we cover. I have no idea so I like to talk to people that have done it before. Founding a company can be lonely so it’s been really helpful to have a co-founder and other founders who get it.

What have you learned about yourself and building a company since founding Leland?

It has been the most intense learning experience of my life by a long shot. You learn everything from the tactical aspects — how to recruit, how to fundraise, how to distribute equity — which are super valuable and you don’t really know them until you do. I think I’ve learned that I am way happier building something and making less money than if I were just going back to a job working for someone else. To feel like we’re in this position where there’s a massive opportunity and it’s up to us to go and execute is amazing. I’ve learned a lot about myself and what matters to me. I enjoy building and creating — I don’t mind being the decision maker and having to fall on the sword if it’s a bad decision.

I’ve also learned a lot about my weaknesses. I think good founders tend to have double edged sword characteristics that can be bad but also make you really valuable as a founder. It’s become very clear that I love to control things as much as I can but I realize that’s a horrible management style. So I’m very conscious of that and if someone else is running at something I’m happy to back off. This has been a good learning experience for me on how to become a better manager and how to inspire people.

How have you grown as a leader since starting Leland?

First and foremost, I take it very seriously. I know people are betting on me and the company with their career so I don’t take that lightly and I want to show up in a way that lets them know that I’m not taking that lightly. One of the stresses of starting a company is that people are investing in you — investors invest their money and employees join companies to grow their careers, so I feel honored to have their confidence and I feel a ton of pressure.

As a leader, it’s really easy to feel that weight every day and anytime something isn’t going well, but I think it allows you to be a better leader because I understand that this is serious.To really internalize that and be comfortable with it, and say you know that’s okay, I’m going to make the most of it and do my best. I think that’s probably been one of the hardest parts.

I think the other piece that I’ve learned is you have to be instilling confidence with everyone you interact with. You can’t be too much of a realist to the point where you’re instilling doubts in people’s heads. How you frame the business in order to inspire confidence is so valuable but it also requires you to be comfortable with not subconsciously hedging. For me, learning how to talk about the business in an inspiring way for my employees and for people around me has been really valuable.

It’s funny because you’ll get off a call with someone you tried to hire and they said no. Then you hop on a call with an investor who just said yes, and then you hop on with an investor who says no. You have to just show up the same every time so that you don’t like carrying that with you because your team will feel it.

What advice would you give to other first-time student founders?

For student entrepreneurs, I think it’s important to understand the tradeoffs of what you’re getting yourself into. It’s really busy and exhausting at times, so make sure that you’re aware that it comes at a cost to certain things and that’s okay.

In terms of advice, I think I would say get started — which sounds super generic. However, l’d say it in the sense of pick one milestone that you know you can hit and go accomplish it. I have so many friends or classmates that have this big startup idea and almost get paralyzed by how many things they think they need to do.

One of the things we did well was be super rigorous around what an MVP is. We ran a couple of tests and got something into the hands of customers so that they can react to it. That process just gives you energy and then you can figure out what the next milestone is. It is helpful to be biased towards action and moving things forward as soon as you possibly can.

People that get MBAs are typically risk averse but it also means that we are fortunate enough to try entrepreneurship and get jobs when we need them. The biggest risk in your life is actually probably not financial risk — it’s probably the risk of not being fulfilled in your life or career. I think a lot of MBAs tend to think about their decision making process in terms of what’s the financial risk and not the whole picture.

I think sometimes people have a hard time turning down all these flashing lights and amazing opportunities that you see in business school but if we think about risk in a different way there’s a more important risk of not doing what I love or not challenging myself.

What does the future of Leland look like?

I’m really excited the next year will be expanding the business to education and career categories beyond MBA admissions, which will be tough but really fun. It will expand Leland’s impact. I get really excited about seeing our customers succeed and empowering coaches to give back and monetize their passion in a meaningful way.

Also, building a team and establishing a company culture that we can be proud of and a place that people love to work is essential for us. We hope to build an enduring company with a great product that impacts the lives of customers, coaches, and the community.

If you’re interested in getting involved at Leland, connect with him on LinkedIn or Twitter. He’s always looking for more people to join the community — feel free to email him.



Glenn is currently a 1st year MBA student at the Massachusetts Institute of Technology, Sloan School of Business and a VC Fellow at Unshackled Ventures.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Glenn Borok

Glenn is currently a 1st year MBA student at the Massachusetts Institute of Technology, Sloan School of Business and a VC Fellow at Unshackled Ventures.