👨‍🏫 Leland: $10,000,000+/yr coaching marketplace playbook

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John Koelliker, a Stanford MBA student at the time, was approached by a friend who wanted to pay him $15K for help getting into b-school.

He took the deal and then built an 8-figure coaching marketplace that flipped an entire industry.

That marketplace is Leland, the coaching platform that just crossed $10M in annual revenue with 2,000+ coaches, 16K+ public reviews. It started with exactly 50 MBA admission coaches and a counter-intuitive strategy that every other marketplace got wrong.

This is a must read if you are interested in building a marketplace business. 

Let’s dive right in 👇.

John wasn't looking to start a company. 

He was a Stanford MBA student who'd gotten into both Harvard and Stanford, and friends kept asking for help with their applications. So he started a little MBA admission consulting business on the side.

But as he ran this business, he saw the marketplace problems up close: low trust, inflated prices, bad actors, and a super fragmented market. It was like a textbook example of everything wrong with an industry, but a PERFECT condition for starting a marketplace business.

The exact moment of clarity came in his Stanford dorm room. John had been noodling on these problems and couldn't stop thinking about them. He realized he might be one of the best people to solve this, given his marketplace experience at Uber, LinkedIn, and Curated (where he'd learned how to match people to experts).

Standing in his dorm room, he thought to himself: "I have to do this."

The world has gotten brutally competitive. When John was applying to college, he'd never heard of admissions consulting. By the time he was applying for business school, it was everywhere. Everything became a competition where expert help actually mattered.

At the same time, COVID accelerated the creator economy. The pandemic normalized remote expertise sharing. People became comfortable both sharing their knowledge online and consuming that expertise through a screen. The number of people starting course businesses and coaching practices exploded.

We will dive into this more in later sections, but here's what John figured out that every other coaching startups got wrong:

John landed on MBA admissions as the initial category due to his proximity to the problem. On top of that, the industry was ripe for disruption. John found dozens of firms charging $10,000+ with minimal technology and no review systems. These traditional firms took 70-80% of what they charged customers while coaches got scraps.

This vertical also had unique advantages as a starting category. It attracted diverse professionals from consulting, banking, product management, tech, healthcare, and etc. So when Leland helped someone get into business school, they naturally got pulled into all those adjacent categories. The perfect vertical for future expansion. 

Leland’s MVP was simple. A marketplace with 50 coaches for MBA admissions.

But the details mattered enormously.

It was a curated group of former admissions officers and successful applicants at various price points, ranging from $30/hour to $400+/hour. 

The value proposition:

Despite the simple platform, client feedback was overwhelmingly positive. The team realized that in a coaching marketplace, the core product is the coaches themselves. The overall experience depends almost entirely on coaching quality. To maintain high standards, John rejected over 90% of coach applicants, a practice that remains today.

The winning formula:

High supply side standard → Good demand side experience → WoM growth

John and his team developed a systematic framework for adding new categories based on customer behavior and network effects.

a) Let user behavior lead the way
Most new category ideas didn’t come from whiteboard sessions. They came from what users were already asking for.

When MBA coaches kept getting questions about startup fundraising, they launched a startup coaching category.

When users wanted help growing freelance businesses, they added that too.

Real data, not assumptions, guided expansion.

b) Follow the customer journey
At the same time, another unlock is the realization that the same customer needs different types of coaching at different stages.

MBA admissions → consulting case prep. Same user, just at a different point in their journey. John built on this by mapping out 30+ common MBA career paths, such as banking, product, tech, healthcare, and expanded categories around those.

c) Focus on 'desperate-to-have' problems

They would prioritize categories that satisfy the following criteria:

These were categories where customers were ready to pay, and coaches could deliver real value.

d) Expand only after trust is built
Leland stayed focused on traditional career coaching until the platform earned enough credibility.

Only then did they branch into newer areas like startup and freelancer coaching—categories where trust matters just as much as expertise.

On the client side, Leland’s growth from 0 to 8 figure revenue was driven mostly by organic channels.

Around 30% came from word of mouth, even before a formal referral program existed. Informal referrals from roommates, siblings, and friends made up nearly half of early growth.

Another 20% came from organic social, especially LinkedIn, where their target audience of ambitious professionals spent time. SEO contributed about 25%, thanks to early investments in content targeting searches like “MBA admissions consulting.”

The rest came from 400+ influencer partners, including accounts like Litquidity and Consulting Humor.

Two other interesting growth strategies stood out in my conversation with John, both centered around the coaches.

a) Free events strategy:

Instead of just connecting coaches with clients, Leland helps coaches build their personal brands and demonstrate their expertise, while driving new customer signups.

Here’s how it works:
Coaches host free events like webinars, Q&A sessions, and workshops focused on their areas of expertise. Leland promotes these events across the platform and their social channels.

These events serve multiple purposes:

Coaches grow their brands and attract clients. Customers get free value and a way to evaluate coaches. Leland benefits from increased traffic, conversions, and engagement.

b) Coach-incentive-led growth flywheel

Besides events, Leland uses smart incentives to turn coaches into growth engines.

When a coach brings their own client to the platform, Leland takes only a 5% cut. If that client later works with another coach, the original coach earns a 5% revenue share 👀.

This setup encourages coaches to bring their own clients to the platform by keeping the take rate low. At the same time, it incentivizes cross-referrals, since coaches continue to earn a share of revenue when their clients choose to work with other coaches on Leland.

Most importantly, it also helps reduce disintermediation by keeping both coaches and clients active and invested in the ecosystem.

The beautiful thing about a marketplace model is that you can quickly expand into different revenue streams once you have reached scale, while maintaining the platform’s core value prop. 

Leland has recently started experimentation with a few new products.

a) Leland Plus 

This subscription product includes video tutorials, sample essays, thousands of resources, all generated by coaches. 

Customers get scalable access to expertise, coaches get additional income streams, and Leland builds recurring revenue. 

b) Enterprise 

Companies like Deloitte and schools like Kellogg wanted to help their people with career development. Instead of individuals paying for coaching, organizations could provide it as a benefit. 

This B2B revenue stream has several advantages: larger contracts, more predictable revenue, and the ability to serve multiple employees from the same organization. It also creates network effects within companies as employees share their coaching experiences with colleagues.

c) Ads and data

Leland is also dabbling in ads and data. 

Many credit unions, recruiting agencies, and other companies have reached out for access to Leland's user base of ambitious professionals. The key here is to be selective and ensure they add value for users on the platform.

Additionally, the rich data signals on the platform create new opportunities. Coaching interactions can provide valuable insights into career trends, skill gaps, and market demands. This data is useful for educational institutions, employers, and other organizations looking to better understand the job market.

Leland can identify which skills are in highest demand, which career transitions are most common, and which coaching approaches are most effective.

1/ Start impossibly narrow, then expand strategically. MBA admissions felt too niche for VCs, but it was the perfect wedge. Don’t try to be everything to everyone from day one. Nail one category first, then follow natural customer connections.

2/ Quality beats quantity every single time. Leland rejects 95% of coaches who apply. Sounds like a terrible growth strategy, but it's what creates trust and network effects. Most marketplaces optimize for quantity of supply, but winners optimize for quality.

3/ Align incentives to prevent disintermediation. When coaches bring clients to Leland, the take rate drops to 5%. If those clients later work with other coaches, the original coach still earns a 5% revenue share. The goal is to deliver so much value to coaches that staying on-platform is the obvious choice.

4/ Follow the customer journey, not your assumptions. Leland's expansion came from what users were already asking for: MBA admissions led to consulting prep, which led to startup coaching. Let customer behavior guide your expansion.

5/ Build multiple revenue streams around the same core asset. Leland expanded from one-on-one coaching to cohort courses, subscription content, enterprise sales, and data insights. The same coaches and customers, multiple ways to monetize. Don't just build a marketplace, build a platform.

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See you next Tuesday 😉,

Leo

p.s. If you are a consumer brand, make sure to check out Highbeam and put your cash to work!

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