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Entrepreneur Q&A with Leland cofounders

· 4 min read
Yiyang Hibner

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How did you form the idea of starting Leland?

John: I’ve always been fascinated by the power that comes from connecting people to people. I saw it up close while building product at Uber, LinkedIn, and Curated (three people-centric marketplaces) and while building my own coaching business. These experiences ultimately led to insight into the expertise economy and the many new trends that were emerging. Once the idea for Leland hit, we knew we had to go after it.

How long did it take to actually hit the ground running?

John: Thankfully, the early team for Leland came together quickly. I called all the most talented people I knew and we got started. Zando and Jiashuo started building the product. Erika ran point on everything coach and customer. Andrew took on growth. I worked on product and pulled together our pre-seed round right around the time we launched, in July 2021. After that, we were off to the races.

What was your biggest fear before full-time committing to start-up life?

Erika: Right before joining Leland, I was working on my own e-commerce company that was growing quickly and had some cool opportunities ahead. When John called me to join the founding team, I had to decide if I'd keep building my online brand, or if I'd take the leap and go all in on Leland. After talking to John (and Zando), catching the vision was simple and my excitement was at an all time high. I felt I would always regret not working with them and building this company together.

So, I wouldn't say there was necessarily “fear” involved with the commitment, I just wanted to make sure I felt confident knowing I was leaving something good behind for something even more incredible. I am beyond sure that I made the right decision — I have never felt more bullish on the impact Leland will have.

What are some areas you are looking to improve as entrepreneurs?

Zando: Part of the fun of building a company is adapting to different needs as the company grows. We’re constantly looking for opportunities to develop ourselves and better serve the needs of the business, whether that’s building our industry knowledge/expertise, enhancing our leadership and management skills, or fine-tuning our communication within the team.

How do you divide tasks as co-founders?

Erika: As co-founders, we frequently discuss what our path forward is and the company strategy, goals, team, and execution plans we need to get there. We have great communication, so it feels natural to know what we need to own together versus what tasks we can divide and take on individually.

Zando does an incredible job running the engineering org and inspiring the team to build quickly and deliver high-quality outputs; our speed and focus is largely due to his influence. I run everything coach, customer, community, and employee — making sure we always provide a world-class experience. John is amazing at holding the whole team accountable, making sure each organization/workstream is prioritizing the right work, running product, and leading the overall direction of the company.

What are some of the biggest challenges you have been facing recently?

John: We’re very lucky to have two important things: (1) an excellent team, and (2) a big market/opportunity. Of course, every day comes with challenges, though. One of Leland’s biggest challenges is learning to build a product and a GTM engine that can support multiple coaching categories. We have coaches in everything from PM to medical school. Of course, there is a lot of overlap in some ways, but there are many differences as well. At first we operated in 1 category, now we have ~10 featured categories, but customers have purchased coaching in ~30 categories.

What does the future of Leland look like?

Zando: Bright! Our ability to both utilize and enable the expertise economy will grow as we expand, providing new opportunities for both sides of the marketplace. We’ll continue to develop and add to our core marketplace dynamics while layering in complementary offerings to address all the parts of helping our customers reach their goals. It won’t be long before Leland is the go-to destination for helping people achieve their career/education/outcome-driven goals.

If our readers want to learn more about Leland, what is your pitch?

We want to help you reach your most ambitious goals! Not only are our coaches are some of the most talented people in the world in their respective fields, they are also genuinely good people who try their best to go above and beyond to help the people they work with. No matter your budget, background, and goals, we’re here to help.

You can get started at or follow us on LinkedIn.