Jason Cohen - Building 2x unicorns scaling, funding, WordPress stagnating and more
Dec 14, 2023
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Jason Cohen, co-founder of WP Engine and a 2-time unicorn founder, shares his startup wisdom at all stages of growth. Topics covered include scaling, funding, WordPress growth, dealing with people challenges at scale, fitting writing into his schedule, and his thoughts on Lemon Squeezy's growth and fundraising. Cohen also discusses the future of WP Engine and gives advice on identifying growth opportunities and understanding the customer base.
Finding balance between regimented routines and pursuing hobbies you enjoy is crucial for personal fulfillment.
Scaling a company requires different strategies and approaches, emphasizing experimentation, adaptation, and willingness to try new approaches.
When considering raising funding, startups should align personal goals, market potential, and self-reinforcing fit in decision-making process with venture capitalists.
Deep dives
The Importance of Focusing on What You Love
In this podcast episode, Jason Cohen discusses the importance of pursuing hobbies and activities that you truly enjoy. He emphasizes the value of turning hobbies into work and the need to find a balance between regimented routines and letting loose. He shares his personal interests in writing, playing the piano, and chess, highlighting the mindset of accepting that it's okay to not excel in every hobby. Cohen encourages individuals to pursue their passions and not to let external pressures or stress interfere with their enjoyment of these activities.
The Challenges of Scaling a Company
Jason Cohen shares his insights on the challenges of scaling a company based on his experiences at WP Engine. He discusses the difficulty of finding information and resources specific to the scaling phase, compared to the abundance of resources available for starting a company. Cohen explores the need for different strategies and approaches when scaling a company, acknowledging that what works in the early stages may not be applicable at scale. He emphasizes the importance of experimentation, adaptation, and a willingness to try new approaches and adjust them as needed when scaling a company.
The Decision to Raise Funding and the Ergodic Nature of Startups
Cohen provides insights on the decision to raise funding and the dynamics between startups and venture capitalists (VCs). He explains that the default path is not to raise funding, and each startup should consider under what circumstances raising money is beneficial. Cohen highlights the misaligned incentives between individual founders and VCs where the potential high rewards for founders are coupled with significant risks, while VCs have a portfolio approach and can tolerate those risks on a broader scale. He advises considering the size and growth potential of the market, the personal goals of the founders, and their alignment with the VC's expected outcome. Cohen also shares the importance of having a self-reinforcing fit within the decision-making process and aligning all aspects of the organization toward a common goal.
Maximizing Options and Building a Good Company
Building a great company that is profitable, growing at a good clip, and has satisfied customers and employees maximizes the options available to the company. By focusing on building a strong company, it becomes possible to make informed decisions about potential avenues for growth, such as going public, raising money, or exploring partnerships. The key is to maintain control over the company's destiny and have the flexibility to choose the best path forward.
Finding the Right Problem to Solve and Leveraging Assets
When considering a new venture, it is important to identify a problem that aligns with the company's assets, talents, and passions. By leveraging these strengths, the company can better position itself to solve the problem and provide value to customers. Additionally, focusing on B2B opportunities rather than B2C can offer advantages, such as a more targeted market, higher potential for revenue, and the ability to tap into existing business networks. Building a good company that solves a real problem and has a strong market fit sets the foundation for long-term success.
Today we’re joined by Jason Cohen. He’s most well known for being the co-founder of WP Engine. You might also know Jason as @asmartbear on Twitter and from his popular blog with the same name, started almost 2 decades ago. Jason is a 2 times unicorn founder so has some incredible startup wisdom at all stages of growth.
This is a wide ranging conversation where we talk about Jason’s day to day life at WP Engine, how he deals with big business problems, if his writing is done on WP Engine, how he would scale to $1m if he was starting from scratch and we also get his thoughts on Lemon Squeezy’s growth going into 2024.
Timestamps
00:00 Intro
02:51 Why there is so little content on the scale up stage
07:00 Is WordPress growth stagnant?
09:47 What does Jason's day look like?
13:02 Doing the boring things
16:08 Does Jason miss the early days?
20:03 Dealing with people challenges at scale
27:56 How does Jason fit writing into his schedule