From Zero to $250 Million: Lessons from a Serial Tech Entrepreneur

Anker Nall's entrepreneurial journey is a testament to the power of persistence, innovation, and seizing opportunities. From humble beginnings as an immigrant student in America to becoming a successful serial entrepreneur, Anker's story offers valuable insights for aspiring business leaders.

Early Entrepreneurial Ventures

While studying at UC Berkeley, Anker stumbled upon an unexpected opportunity - building Facebook apps. This was in the early days of the Facebook platform, when viral growth was still possible:

"It started my freshman summer when they launched the Facebook platform. At first there were silly apps that would make 10 bucks a day, 20 bucks a day, but it was a crazy time because you could literally reach millions of people in 24 hours."

Through experimentation, Anker found formats that worked, like quizzes that people would repeatedly take and share. At its peak, his Facebook app business was generating $50,000 per day and had more daily active users than major websites like LinkedIn.

This early success taught Anker valuable lessons about viral marketing and rapid growth that would serve him well in future ventures. It also provided the financial cushion that allowed him to pursue entrepreneurship full-time after college.

Building and Selling Teachable for $250 Million

After a few years of trying different business ideas, Anker started Teachable (originally called Fedora) as a side project. The platform allowed creators to build and sell online courses.

Unlike his previous attempts, Teachable showed immediate traction:

"The first month we processed maybe like $3,000 in course sales but every single month after that we processed a little bit more until eight or nine months in we were doing $450,000 a month in course sales across I want to say 15-20 creators and I was like wow there may be a real business here."

Anker moved to New York, raised venture capital, and grew Teachable into a major player in the online education space. In March 2020, he sold the company for a reported $250 million.

Interestingly, the deal closed during the stock market crash at the beginning of the COVID-19 pandemic. While this timing was nerve-wracking, it also led to unexpected growth:

"We saw our biggest signup and revenue days at Teachable because this was the opposite sort of trend where our business - like we sold the company at about 25 million in ARR and we doubled to 50 million 3 months later."

Key Lessons for Entrepreneurs

Through his experiences building multiple companies, Anker has developed several insights that can benefit other entrepreneurs:

1. Focus on execution over planning

Anker emphasizes the importance of taking action rather than getting stuck in analysis paralysis:

"The amount of people I've spoken to that are constantly stuck in the analysis paralysis stage of like trying to find the perfect idea, find the perfect brand name, trying to find the perfect logo versus just going out there putting yourself out there, asking someone for money and doing the thing - that's really what it comes down to."

2. Be willing to move fast and make mistakes

Speed of execution is a key advantage for startups competing against larger companies:

"I'd rather have a frenetic pace of execution even if you make more mistakes because for our kind of company speed is one of the only advantages we have. So I index a lot in people who move really fast."

3. Solve your own problems

When choosing what business to start, Anker recommends focusing on problems you've personally experienced:

"If you were a friend telling me I want to start a company how do I maximize my chances of even getting funded I would say solve your problem. You already know who to build for, it's easier to find customers."

4. Don't undervalue your offerings

With Teachable, Anker found that many creators underpriced their courses. He advises:

"Even though this sounds crazy, double your price and work backwards. Let's say you double your price, you there's no way it's worth that. Okay, what would you have to change to make it be worth that price?"

5. Hire for startup fit, not just pedigree

In hiring, Anker now focuses less on prestigious backgrounds and more on finding people who truly want the startup experience:

"Finding someone who uniquely wants to be at a startup and wants that kind of challenge has been much better."

6. Be prepared for the mental challenges

Building a startup is extremely demanding, and Anker cautions founders to expect significant stress:

"If you're going to do a startup, especially a venture-backed startup, expect massive mental pain. Just expect it. And if you don't want that, that's very healthy of you honestly, probably better. It's just that there's a sense of fiduciary responsibility."

The Next Chapter: Building Carry

After selling Teachable, Anker didn't rest on his laurels. He's now building Carry, a fintech startup focused on helping individuals and businesses optimize their taxes and build wealth.

Carry represents a new challenge for Anker - building in a highly regulated industry:

"We are a regulated organization, we're going to be a broker-dealer. Even if AI makes it really easy to do stuff, the SEC is not going to approve people in two days, FINRA is not going to approve people in two days. So regulatory moats I think are going to be real and will continue being real even as everything else gets faster."

While the business is still young, Anker is excited about the potential to have an even bigger impact than with Teachable:

"We're trying to long-term compete with Vanguard, Schwab, Fidelity and these companies that are anywhere from 40 to 100 years old and we're fine if it takes a little bit longer."

Conclusion

Anker Nall's journey from college side-hustler to successful serial entrepreneur offers valuable lessons for anyone looking to build a business. His emphasis on rapid execution, solving real problems, and being prepared for the mental challenges of startup life are particularly salient.

As he builds his next venture, Anker remains driven by the thrill of creation and competition:

"It's like other sports - if someone is a great tennis player or whatever, not going to retire at 31 or 32, they want to do this for another 5 years, 10 years. It's a thing that gives me joy, very competitive person and it's my arena and place to compete."

For aspiring entrepreneurs, Anker's story demonstrates that with persistence, adaptability, and a willingness to take calculated risks, it's possible to build multiple successful businesses from scratch. The key is to start building, learn from both successes and failures, and keep pushing forward.

Article created from: https://www.youtube.com/watch?v=8eK4ic7_M_U