Leland puts a price on the right advice

Before there was a marketplace, there was an awkward conversation. Someone wanted help getting into business school. Someone else knew how to help. Then came the delicate business of discussing money. For the people who would build Leland, this was a recurring problem: expertise existed, demand existed, yet arranging an exchange remained surprisingly clumsy.

First came the awkward conversation

Leland’s founding account describes coaches struggling to reach people and applicants struggling to find, evaluate, and afford help. Some applicants resorted to hundreds of cold emails. The first thing straining was the informal arrangement: a useful contact here, a favor there, and no reliable way to make the whole process repeatable.

The early team had more than a theory. Their separate coaching side businesses collectively earned over $100,000 in 2020. That was evidence of willingness to pay, before there was a platform to pay through. Building began in January 2021; the marketplace launched that July.

John Koelliker, now CEO, had worked in product at Uber, LinkedIn, and Curated. Erika Mahterian, identified alongside him as a cofounder by Forbes, brought an interest in education and mentorship. In her account of joining, she described school applications as a process people needed an army of support to navigate.

The MBA was the opening move

The initial category was deliberately narrow: MBA admissions. An applicant had a recognizable goal, an approaching deadline, and questions that someone a few steps ahead could answer. The expert’s own experience was relevant. An admissions essay, after all, comes with rather more personal baggage than an instruction manual.

By May 2022, Leland said it had more than 100 coaches and had sold over 2,500 coaching hours in nine months. It announced a $4 million seed round and eight additional categories. The clever part was the supply: people who understood MBA admissions often also understood consulting, finance, or technology recruiting.

That gave expansion a practical logic. The same person could help with the school application and, later, the interview. Leland could organize expertise around the customer’s next decision. For anyone building a marketplace, this is a useful sequence to copy: begin with a specific purchase, then look for adjacent problems the existing experts can solve.

Follow the fee

A customer now encounters profiles, reviews, hourly rates, packages, and introductory calls. One public consulting coach profile, Yuyun Liang’s, lists $99 an hour and a 20-hour package at $1,683. Those are examples, not a platform-wide tariff. Experts set their prices, so an applicant can buy a focused intervention rather than assume every problem requires a comprehensive engagement.

Behind that transaction is another customer: the coach. Leland supplies discovery, scheduling, and payments. Its June 2026 payout guidance makes the exchange explicit. When experts bring clients themselves, the platform fee is 5%, plus processing. For platform-generated leads that experts convert, it starts at 20% and falls as that client buys more coaching.

Sales-assisted leads carry an additional 10% sales fee; partner arrangements can differ. These details matter because “a marketplace” sounds like one business model. Here, the margin depends on who does the work of finding and converting the customer.

The competitive position sits between an admissions consultancy, a tutor directory, and employer-funded professional development. A specialist consultancy sells its own approach. Leland lets buyers choose among independent experts. Free alumni mentoring remains a sensible alternative when the right person is available; Leland’s proposition is making that search more organized and purchasable.

That choice also changes what expertise means. An admissions adviser may know how to sharpen an application; a working consultant may be especially useful for a practice case. Neither credential automatically answers the other question. A customer has to distinguish between recognition, relevant knowledge, and the ability to teach it. Profiles and reviews make that distinction easier to investigate, but the buyer still has work to do.

The next application is an AI workflow

In November 2024, Forerunner led Leland’s $12 million Series A. The company said it entered the fundraise cash-flow positive. Its stated plans included more content, courses, partnerships, and enterprise opportunities. The product was already becoming bigger than a calendar of individual appointments.

By March 2026, that expansion had acquired a new subject: AI. Leland announced its AI Builder Program for professionals whose jobs were changing. “We refuse to let people be left behind,” Koelliker said. The company frames the curriculum around making things people can use at work.

“We refuse to let people be left behind.”John Koelliker · March 2026

The current individual offer costs $1,499, with a two-week live component, further course material, and support. Exercises include building a product, automating communication, and analyzing data. Some sessions benefit from additional paid AI subscriptions. Employers can also buy training, custom workflow implementation, and help recruiting people who build with AI.

This is a substantial extension of the original marketplace. Selling an hour with an expert and deploying a workflow inside a business require different delivery. The connection is the customer’s predicament: a consequential transition, unfamiliar rules, and a need for someone who can turn general information into a concrete next step.

Universities provide another route to those customers. Leland’s homepage describes a Kellogg partnership offering career coaching across consulting, technology, and finance. The institution can organize access around its students’ recruiting needs. Alongside live courses and the Leland+ resource library, it creates several ways into the same network: browse independently, learn with a group, or receive support through an organization.

Buy a smaller problem

The sensible way to use Leland is to arrive with something specific: an essay draft, a case interview weakness, a résumé, or a repetitive work task. Compare relevant experience, ask what the session will produce, and use an introductory call where available. A famous employer on a profile is a clue; the fit between the expert’s knowledge and your problem deserves closer attention.

Coaching still depends on judgment, preparation, and follow-through. A marketplace cannot create a job opening or an admissions place. Leland’s first-session policy provides conditional rematching after a timely complaint, rather than a promised outcome. The useful purchase is help with a decision or a skill you can act on. Start there, and the value of the next hour becomes easier to judge.