The Hardest Part of Building a Two-Sided Platform

When I launched Upnotch, I had a clear vision of what it needed to be.

A place where any professional in the world could find a mentor. Where anyone with experience and wisdom to share could offer it to someone who needed it. A community built around the kind of human connection that had changed my own career and that I knew most people were not getting access to.

What I did not fully anticipate was the specific kind of problem I had just signed up to solve.

The problem nobody warns you about

Building a platform where the value comes entirely from other people is one of the most humbling experiences in business.

Not because it is impossible. But because you cannot create the value yourself. You can build the best product in the world, design the most intuitive experience, write the most compelling copy — and none of it matters if the people who need to show up on both sides are not there yet.

For Upnotch to work, mentors and mentees both needed to be present. Mentees needed enough mentors to find the right match. Mentors needed enough mentees to make showing up feel worthwhile. Without both sides, there was no platform. There was just a very well designed empty room.

That is the chicken and egg problem. And living inside it is a very different experience from reading about it.

What it actually felt like

In the early days I would wake up thinking about the same question.

Which side do you build first?

If I focused on recruiting mentors, I had a growing supply of people ready to help with nobody to help yet. If I focused on bringing in mentees, I had people looking for guidance with nobody to guide them. Every decision felt like it was solving half the problem while creating the other half.

I tried things that did not work. I adjusted. I tried again. There were stretches where I genuinely could not tell if the platform was gaining traction or if I was just getting better at staying busy.

What made it harder was that the value of the platform was invisible until it was not. Until a mentee found exactly the right mentor at exactly the right moment. Until a mentor had a conversation that reminded them why sharing what they had learned mattered. Those moments were real and they were powerful but in the early stages they were rare enough that you had to hold onto them tightly on the days when nothing seemed to be moving.

The second layer nobody talks about

Just when I felt like I was beginning to understand the mentor and mentee dynamic, I realized there was another version of the same problem operating underneath it.

Individual professionals and organizations needed different things from the platform. An individual coming to Upnotch was looking for a mentor who understood their specific situation, their industry, their goals. The value was personal and immediate.

An organization coming to Upnotch was looking for something structural. A way to build mentorship into their community at scale, track participation, demonstrate outcomes, and create something sustainable. The value was systemic and longer term.

Same platform. Two completely different definitions of success.

Building for both simultaneously meant that every decision about product, messaging, and priorities had competing right answers depending on which side of the platform you were standing on. What made the individual experience better did not always make the organizational experience better. And what organizations needed to justify the investment was not always what individual professionals needed to feel the value.

I had to learn to hold both realities at the same time without letting either one collapse.

What finally gave me direction

The thing that helped most was not a framework or a strategy. It was going back to the reason I built the platform in the first place.

I built Upnotch because I had struggled to find mentorship myself. Because I knew firsthand what it felt like to be trying to grow something, hitting walls you cannot see around, and not having the right person to turn to. I built it because a career is never built alone and too many people were trying to build theirs without the support they needed.

That clarity did not solve the chicken and egg problem overnight. But it told me which side to prioritize first.

Start with the mentee. Build for the person who needs help. Make it as easy as possible for them to find the right person, have the right conversation, and experience the kind of value that makes them come back and tell someone else.

If the experience is real enough, the mentors follow. And if the mentors are having meaningful conversations, the organizations start to see what is possible.

That is not a perfect strategy. But it is an honest one. And on the days when nothing seemed to be working, having a clear answer to why I was building this and for whom was the thing that kept me from walking away.

What two-sided platforms actually require

If you are building something where the value depends on two groups showing up for each other, there is something I wish someone had told me earlier.

You cannot force both sides to grow at the same pace. You can create conditions that make each side more likely to show up. You can reduce the friction, improve the experience, make the value clearer. But ultimately you are building something that requires other people to believe in it before it has fully become what you know it can be.

That requires a different kind of patience than most things in business. Not passive patience. Active patience. Showing up every day to build the conditions for something that has not fully arrived yet, holding onto the moments when it works, and being honest with yourself about what is not working so you can keep adjusting.

If this was easy, everybody would do it.

The fact that it is hard is not a reason to stop. It is a reason to stay close to why you started.