Steven Cox wanted to keep the drummer

The drummer was going to leave. Steven Cox could afford to play in a band for enjoyment; his bandmate Enrique needed it to pay the bills. There was a baby coming, and a restaurant job offered something music had failed to provide: a dependable income. The problem with having a passion is that the landlord tends to prefer money.

Cox knew Enrique could play. He knew he could teach, too. What Enrique struggled with was finding enough students. Posters in local shops had limited powers of persuasion. Cox asked about using the internet. His friend understood music better than marketing, which seemed a reasonable division of expertise until one had to make a living from the other.

Helping him became a project, then a company. Founded in 2006, TakeLessons would connect instructors with people who wanted to learn. Its eventual sale to Microsoft in 2021 makes a tidy business milestone. The more revealing detail is smaller: Cox kept returning to the question of whether a talented person could afford to continue doing the work.

The company began in a spare bedroom overlooking Mission Beach in San Diego. It is an agreeable address for an origin story, although an ocean view does surprisingly little of the coding. Cox put in his own money and worked through the early versions. He had found a problem close enough to hear from the next seat in the band.

Gospel, finance, and a rental van

Long before he was arranging lessons, Cox was surrounded by music. He grew up in Dayton, Ohio, in a family that sang and played gospel. His grandparents and parents made records. He played bass and sang, later performing in bands and working as a DJ during college. Music was ordinary family activity before it became a market to examine.

At Eastern Kentucky University he studied investment finance and human communication, graduating with honors. The pairing feels unusually well suited to his later work: one subject asks what the numbers mean, the other asks whether anybody understands you. He would spend much of his career moving between those questions.

His childhood also gave financial security a particular urgency. Cox has described growing up poor and wanting a different future. In his account of the first internet boom, a friend's invitation to join a business out west led to a rapid departure from his existing job. He packed his possessions into a rental van and went.

He became an early employee at PurchasePro, the business-to-business ecommerce company that went public in 1999. The ride supplied experience of expansion and of the limits of paper wealth. He later worked at CollegeClub.com, an early social network, and ran the internet consulting firm Reddito. By the time he began TakeLessons, he had already seen businesses from several uncomfortable angles.

The appointment was the product

An instructor with an empty afternoon and a student with a free afternoon ought to be able to find one another. Insert a subject, a location, a price, a timetable and a little uncertainty about strangers, however, and the apparent simplicity begins to unravel. A lesson is a surprisingly complicated appointment.

TakeLessons worked on the surrounding chores. Students could find teachers; instructors could use scheduling, billing, payment and communication tools. The point was to let expertise travel further than the teacher's own ability to advertise it. A good musician should not need a second qualification in collecting invoices.

Cox's early team learned by getting close to instructors. They brought teachers aboard individually, listened to their accounts of the working day and watched lessons. In his telling, those deliberately laborious beginnings helped the team understand what people would use. A business intended to operate through screens first needed people sitting beside one another.

By 2019, Cox was describing a service spanning roughly 300 subjects, with private and group instruction available online as well as in person. Teachers set their private-lesson prices. The catalogue extended beyond music into languages, academic tutoring and software skills. The relationship with an actual instructor remained central: someone could listen, respond and notice where a learner was getting stuck.

There is a personal logic to that design. Cox had experienced the difference between playing music for fun and needing it to produce income. His company occupied the space between those two versions of the same activity. The teacher still had to teach. The platform was supposed to make the next lesson easier to arrange.

A modest camera, a widening stage

Cox's approach to promoting the business sometimes looked like a musician's approach to finding an audience. TakeLessons filmed student recitals, allowing learners to show what they could do. A 2009 account described a $150 Flip camera and videos of first public performances. The equipment budget was modest; the occasion mattered to the people on screen.

Teachers also wrote for the company's blog, sharing their knowledge while gaining exposure. Cox described the approach neatly: “We try to talk less about us and more about them.” That is an appealing instruction for a company built around other people's abilities. It also leaves rather less room for the CEO's inspirational headshot.

Investment brought room to expand. In 2011, TakeLessons announced a $6 million round led by Crosslink Capital, with Eric Chin joining the board. Its announcement described instruction in more than 2,800 American cities and a partnership putting lessons inside Best Buy stores. Teaching could sit beside the equipment that made a customer want to learn.

In March 2014, Cox announced another $7 million, bringing the total raised at that point to $20 million. He said the instructor roster had tripled over the preceding year. Tutoring, languages and performing arts were part of the expansion; welding, crocheting, robotics and basic HTML were appearing among the matches. The band had acquired quite an eclectic repertoire.

The income they chose to lose

Growth did not make every decision easier. One early experiment placed Google advertisements inside search results. The clicks generated money when money was scarce. Then co-founder Chuck Smith said he was not proud of what they had built: people were clicking without understanding what they were clicking on. The team removed the ads after a few days.

Cox used the episode to explain a company value: “Build things you’re proud of.” It is a pleasant sentiment until keeping it requires abandoning revenue. Here it came with a cost attached. He also acknowledged mistakes, including launching too broadly and trusting the team's own confidence more than customer evidence.

His writing about employees offered another test of those values. When August Mao left TakeLessons to pursue acting in Los Angeles, Cox published his goodbye and wished him well. He wanted people to acquire skills, friendships and confidence while working at the company, even if their next ambition took them elsewhere.

That is a slightly awkward aspiration for an employer. Help someone grow sufficiently and they may grow towards the door. Cox nevertheless argued that a workplace should provide something people could carry with them. Mao's departure made the argument concrete: an employee could leave for a creative life and still be treated as part of the company's story.

“Build things you’re proud of.”

Steven Cox / a TakeLessons value

What an exit leaves behind

Selling TakeLessons took a different kind of judgment. Cox later described exploring acquisition interest in 2012 and deciding there was more to build. Other periods brought a willingness to sell without a willing buyer. During the surge in online learning in 2020 and 2021, the company tested interest again. Timing had opinions of its own.

Microsoft acquired the company in September 2021. The price was not disclosed. Cox described a fit between the buyer's plans and what TakeLessons had built, rather than a deal dependent on persuading an outsider to become interested in the entire category. He also emphasized a practical outcome: the employees had Microsoft jobs after the transaction.

In May 2022, he announced that he was leaving full-time work at TakeLessons and Microsoft for a consulting role. His farewell dwelt on teachers who had written to say they could pay their student loans, afford an apartment or reach students abroad. After years of funnels and code, those were the results he chose to remember.

He subsequently made the case for acquisitions in public policy. In an August 2023 opinion piece, he argued that exits help finance the next generation of businesses and said he had invested some of his proceeds in six early-stage companies. The money had begun another journey, this time with him on the investor's side of the conversation.

The service itself had a later ending. TakeLessons closed on November 15, 2024. Microsoft's closure guidance addressed unfinished payments, refunds and access to account records. That date belongs beside the acquisition date in any account of the business. A founder's successful sale and a platform's continuing availability are separate events, with different consequences for the people involved.

Back on the other side of the lesson

Cox's own next chapter has taken him towards performance. His acting site places him in Beverly Hills and presents work for screen, commercials and theatre. It lists study with Aaron Speiser and Kay Aston and describes more than 2,000 hours spent in acting classes. A film reel is labeled September 2025. The former lessons executive has put in considerable time taking lessons.

The turn has roots. Church plays, bands and records preceded the company. His personal biography describes two alternative rock albums and the pleasure of learning that a couple had chosen one of his songs for their wedding dance. Alongside business, he has also pursued photography, including an image used for HGTV's Hot Properties San Diego.

There is a pleasing lack of efficiency in returning to a craft after a business career. You have to attend, practise and accept instruction. A sale can change your bank balance; it offers no exemption from learning a scene. For someone who built a marketplace around the value of teachers, that seems a fair arrangement.

Enrique never took the restaurant job, Cox wrote in 2023. It remains a small, legible outcome in a career crowded with larger numbers. One musician stayed with music. Years later, the friend who helped him was making room for creative work of his own. The drummer kept his place. Cox found another part to learn.