Happy Hanukkah! Did you know I recorded this song for the holidays?
Disclaimer: the author is not a financial adviser. Consult with a tax advisor for your country’s specific laws. NFA. DYOR.
As of May 2025, Andrew Wilkinson’s net worth is around $400M. His book is titled: Never Enough: From Barista to Billionaire.
Last week on Methods of Prosperity
Brian had been interim CEO of MetaLab for a while. Then he raised Andrew’s suspicions.
Upon investigation, Andrew discovered Brian was embezzling company funds. Brian was planning to start a rival agency.
Andrew and Chris gathered evidence to build a strong case against Brian. They backed up emails and documented Brian’s attempts to delete incriminating information. Finally, catching Brian attempting to steal a client, they fired him.
It was an arduous legal battle. Brian sued them for $15 million. His defense didn’t hold up against scrutiny. They settled for $100,000.
Andrew resumed the role of CEO. He sought to streamline operations by avoiding what he disliked.
Andrew and Chris focused on investing, interested in acquiring Dribbble – a platform for designers to share their work in progress and get feedback from the community.
Dan Cederholm wrote the book that Andrew learned web design from. He’s co-founder of Dribbble. But Dan wasn’t interested in selling.
Until one day, the phone rang.
The following is Methods of Prosperity newsletter number 95. It was originally deployed April 10, 2025. As of December 18, 2025, original subscribers have received up to Methods of Prosperity newsletter no. 131: Marc Rowan.
Methods of Prosperity newsletter is intended to share ideas and build relationships. To become a billionaire, one must first be conditioned to think like a billionaire. To that agenda, this newsletter studies remarkable people in history who demonstrated what to do (and what not to do). Let me know how I can help you out. For more information about the author, please visit seanallenfenn.com/FAQ.
95
Key Lessons:
Graduate from self-employed to investor.
Be the buyer you’d want to sell to.
Acknowledge your motives.
Own a holding company.
Be persistent.
Advertisement:
Owning a home now costs $52K more per year than renting. Families are stuck as forever renters. We’re seizing this shift. Buying 100+ unit assets in growth markets.
Few get in.
Accredited investors can gain access at inveresta.com
We’re improving quality of life at scale for hard working families.
This is not an offer, solicitation of an offer, to buy or sell securities. Past performance is not an indication of future results. Investing involves risk and may result in partial or total loss. Prospective investors should carefully consider investment objectives, risks, charges and expenses, and should consult with a tax or legal adviser before making any investment decision.
Andrew’s phone rang. It was Dan calling. Andrew had been bugging him to sell Dribbble. Dan wasn’t motivated to sell their social network, Dribbble. Neither was Dan’s co-founder, Rich. They were accidental entrepreneurs who built a social network for graphic designers. Any successful social network has a moat. If all the good graphic designers use it, there’s not much competition. That’s power law distribution. All graphic designers gravitated to it.
Dan called Andrew because he and Rich changed their minds. They wanted to discuss the idea. Andrew and Chris flew to Boston to meet with them a week later. Dan and Rich loved working on the business, but they were too busy working in the business. They loved design. Managing employees and making calls to solicit advertisers was not enjoyable. Andrew and Chris shared with them their list of their “anti-goals”. Andrew explained, “We’d take care of what you hate so you can focus on what you love.”
Andrew and Chris understood what Dan and Rich wanted. Their unique experience selling Pixel Union gave them the insight. They became the buyer that they wished they had. Andrew and Chris would preserve the integrity of what Dan and Rich built. They offered to buy a majority stake of the business for a high 7 figure valuation. At the time, Dribbble was only doing around $2 million in annual revenue. Andrew and Chris recognized the levers they could pull to increase it to $10 million.
Dan and Rich agreed, but it was going to cost several million dollars more than Andrew and Chris had in cash. It had to be a leveraged buyout on a recourse loan. That means Andrew and Chris had personal liability. If the bank had to foreclose, they’d be bankrupt. Still, they were confident. Their plan was to execute on their growth strategy and build the ad sales team. It was realistic and achievable with low downside risk.
That’s when Andrew and Chris set up their holding company and named it Tiny. Tiny acquired Dribbble in January 2017 for $5.5 million, securing a 70% stake in the business. They recruited Zack Onisko, a designer and former co-founder of Creative Market. He joined Dribbble as CEO in 2017. Zack built out the ad sales team, expanded services, and grew the company before stepping down in 2024.
Tiny repurchased Pixel Union on April 1, 2019, leading an investment round. This was alongside Freemark Partners, Saltwater, and Syrus Partners. Tiny reacquired Teligence Capital’s majority stake in the company. This marked Tiny’s return to majority ownership. Andrew and Chris sold Pixel Union to Teligence Capital in 2014 (with Brian’s help). The 2019 deal included a commitment of $25 million CAD. This was to acquire additional Shopify ecosystem businesses. Pixel Union’s CEO, Ben Moore, retained leadership, focusing on expanding Shopify-centric services. The move aligned with Tiny’s strategy to invest in e-commerce infrastructure.
Tiny acquired AeroPress in summer 2021. The AeroPress is a manual coffee maker. It uses air pressure to speed the filtering process. Alan Adler designed the AeroPress to minimize the bitterness of the coffee. Adler sold for $70 million. He retained a minority stake and continued involvement in operations. Tiny allocated funds for R&D, and new product innovation. They expanded the AeroPress Go line. They provided global marketing, scaling the brand. Tiny preserved its quality and community-driven ethos. The acquisition aligned with Tiny’s strategy. Investing in niche, profitable businesses with strong cultural followings.
It was around that time that a mutual friend introduced Andrew and Chris to Charlie Munger. Andrew Marks, the son of famed investor Howard Marks. Marks Jr said that Munger had a problem and that Andrew could help him. The Daily Journal is an old-school software company Munger chaired. The Daily Journal Corporation is a U.S.-based company. It specializes in publishing and technology, serving the legal and business sectors. Charlie Munger acquired it in 1977. He expanded its reach.
Andrew and Chris met with Charlie Munger in his home. They explained their business to him. In Andrew’s words, Munger seemed like a “stone statue”. Andrew couldn’t tell if Munger was “unimpressed, or bored, or what.” He finally caught Munger’s attention after he said: “We have no intent on ever going public.” Munger said “[being public] creates a slew of opportunities.” and proceeded to explain the benefits of being a public company.
Andrew’s version of the story is this. Charlie Munger then said, “You know, there's another way for you to go public.” Andrew replied, “What’s that?” Munger said:
“Well, somebody needs to take over for us at The Daily Journal. We could just merge our companies and you two could take the reins. You have all these wonderful technology businesses, and we have hundreds of millions of dollars that need investing and a software business that could use your expertise.”
The merger didn’t go through. Chris Sparling’s version of the story is this. They realized that their ego was driving the decision. They wanted to become successors to their idol rather than providing actual help. Acknowledging this, they decided to introduce Munger to Steven Myhill-Jones. Munger appointed Steven as CEO of The Daily Journal.
Conclusion: Andrew and Chris went from agency owner/operators (self-employed) to investors. The fact is that it’s not likely that you will build substantial wealth unless you own assets. Building wealth through a holding company can be a smart, strategic move. This is a parent entity that owns enough stock or assets in other companies (subsidiaries). The parent company controls its subsidiaries. You don’t have to involve yourself in their day-to-day activities. Delegate it to a CEO. Buy another company. Hire a CEO. Rinse and repeat.
A holding company is usually an LLC or corporation. It doesn’t produce goods or services itself. Its primary role is to own and manage investments. Such as shares in operating companies, real estate, or intellectual property. You can set up multiple subsidiaries and have the holding company own them. For example, you start a marketing agency and a software company. Each is its own entity, but your holding company owns both of them.
Imagine you set up “WealthHold Co.” You buy a small rental property business ($500k revenue/year). You buy a niche e-commerce store ($200k revenue/year). They’re subsidiaries. WealthHold Co. owns 100% of both. The rental business pays dividends to WealthHold, which you use to buy a third subsidiary. Your third subsidiary could be a local service company. Over 10 years, the combined value grows, and you sell WealthHold Co. for millions, or keep it as a passive income machine.
I like you,
– Sean Allen Fenn
PS: The purpose of wealth is freedom. You can have financial freedom, but not by yourself. That’s why we’re building our core group of people. It’s a community to help each other achieve financial freedom. One way is by pooling our resources to invest in Multifamily real estate together. Whatever method of prosperity you choose, don’t go at it alone. You can now join our Methods of Prosperity community on Telegram here:
Community
Subscribe to seanallenfenn.eth
<100 subscribers
Happy Hanukkah! Did you know I recorded this song for the holidays?
Disclaimer: the author is not a financial adviser. Consult with a tax advisor for your country’s specific laws. NFA. DYOR.
As of May 2025, Andrew Wilkinson’s net worth is around $400M. His book is titled: Never Enough: From Barista to Billionaire.
Last week on Methods of Prosperity
Brian had been interim CEO of MetaLab for a while. Then he raised Andrew’s suspicions.
Upon investigation, Andrew discovered Brian was embezzling company funds. Brian was planning to start a rival agency.
Andrew and Chris gathered evidence to build a strong case against Brian. They backed up emails and documented Brian’s attempts to delete incriminating information. Finally, catching Brian attempting to steal a client, they fired him.
It was an arduous legal battle. Brian sued them for $15 million. His defense didn’t hold up against scrutiny. They settled for $100,000.
Andrew resumed the role of CEO. He sought to streamline operations by avoiding what he disliked.
Andrew and Chris focused on investing, interested in acquiring Dribbble – a platform for designers to share their work in progress and get feedback from the community.
Dan Cederholm wrote the book that Andrew learned web design from. He’s co-founder of Dribbble. But Dan wasn’t interested in selling.
Until one day, the phone rang.
The following is Methods of Prosperity newsletter number 95. It was originally deployed April 10, 2025. As of December 18, 2025, original subscribers have received up to Methods of Prosperity newsletter no. 131: Marc Rowan.
Methods of Prosperity newsletter is intended to share ideas and build relationships. To become a billionaire, one must first be conditioned to think like a billionaire. To that agenda, this newsletter studies remarkable people in history who demonstrated what to do (and what not to do). Let me know how I can help you out. For more information about the author, please visit seanallenfenn.com/FAQ.
95
Key Lessons:
Graduate from self-employed to investor.
Be the buyer you’d want to sell to.
Acknowledge your motives.
Own a holding company.
Be persistent.
Advertisement:
Owning a home now costs $52K more per year than renting. Families are stuck as forever renters. We’re seizing this shift. Buying 100+ unit assets in growth markets.
Few get in.
Accredited investors can gain access at inveresta.com
We’re improving quality of life at scale for hard working families.
This is not an offer, solicitation of an offer, to buy or sell securities. Past performance is not an indication of future results. Investing involves risk and may result in partial or total loss. Prospective investors should carefully consider investment objectives, risks, charges and expenses, and should consult with a tax or legal adviser before making any investment decision.
Andrew’s phone rang. It was Dan calling. Andrew had been bugging him to sell Dribbble. Dan wasn’t motivated to sell their social network, Dribbble. Neither was Dan’s co-founder, Rich. They were accidental entrepreneurs who built a social network for graphic designers. Any successful social network has a moat. If all the good graphic designers use it, there’s not much competition. That’s power law distribution. All graphic designers gravitated to it.
Dan called Andrew because he and Rich changed their minds. They wanted to discuss the idea. Andrew and Chris flew to Boston to meet with them a week later. Dan and Rich loved working on the business, but they were too busy working in the business. They loved design. Managing employees and making calls to solicit advertisers was not enjoyable. Andrew and Chris shared with them their list of their “anti-goals”. Andrew explained, “We’d take care of what you hate so you can focus on what you love.”
Andrew and Chris understood what Dan and Rich wanted. Their unique experience selling Pixel Union gave them the insight. They became the buyer that they wished they had. Andrew and Chris would preserve the integrity of what Dan and Rich built. They offered to buy a majority stake of the business for a high 7 figure valuation. At the time, Dribbble was only doing around $2 million in annual revenue. Andrew and Chris recognized the levers they could pull to increase it to $10 million.
Dan and Rich agreed, but it was going to cost several million dollars more than Andrew and Chris had in cash. It had to be a leveraged buyout on a recourse loan. That means Andrew and Chris had personal liability. If the bank had to foreclose, they’d be bankrupt. Still, they were confident. Their plan was to execute on their growth strategy and build the ad sales team. It was realistic and achievable with low downside risk.
That’s when Andrew and Chris set up their holding company and named it Tiny. Tiny acquired Dribbble in January 2017 for $5.5 million, securing a 70% stake in the business. They recruited Zack Onisko, a designer and former co-founder of Creative Market. He joined Dribbble as CEO in 2017. Zack built out the ad sales team, expanded services, and grew the company before stepping down in 2024.
Tiny repurchased Pixel Union on April 1, 2019, leading an investment round. This was alongside Freemark Partners, Saltwater, and Syrus Partners. Tiny reacquired Teligence Capital’s majority stake in the company. This marked Tiny’s return to majority ownership. Andrew and Chris sold Pixel Union to Teligence Capital in 2014 (with Brian’s help). The 2019 deal included a commitment of $25 million CAD. This was to acquire additional Shopify ecosystem businesses. Pixel Union’s CEO, Ben Moore, retained leadership, focusing on expanding Shopify-centric services. The move aligned with Tiny’s strategy to invest in e-commerce infrastructure.
Tiny acquired AeroPress in summer 2021. The AeroPress is a manual coffee maker. It uses air pressure to speed the filtering process. Alan Adler designed the AeroPress to minimize the bitterness of the coffee. Adler sold for $70 million. He retained a minority stake and continued involvement in operations. Tiny allocated funds for R&D, and new product innovation. They expanded the AeroPress Go line. They provided global marketing, scaling the brand. Tiny preserved its quality and community-driven ethos. The acquisition aligned with Tiny’s strategy. Investing in niche, profitable businesses with strong cultural followings.
It was around that time that a mutual friend introduced Andrew and Chris to Charlie Munger. Andrew Marks, the son of famed investor Howard Marks. Marks Jr said that Munger had a problem and that Andrew could help him. The Daily Journal is an old-school software company Munger chaired. The Daily Journal Corporation is a U.S.-based company. It specializes in publishing and technology, serving the legal and business sectors. Charlie Munger acquired it in 1977. He expanded its reach.
Andrew and Chris met with Charlie Munger in his home. They explained their business to him. In Andrew’s words, Munger seemed like a “stone statue”. Andrew couldn’t tell if Munger was “unimpressed, or bored, or what.” He finally caught Munger’s attention after he said: “We have no intent on ever going public.” Munger said “[being public] creates a slew of opportunities.” and proceeded to explain the benefits of being a public company.
Andrew’s version of the story is this. Charlie Munger then said, “You know, there's another way for you to go public.” Andrew replied, “What’s that?” Munger said:
“Well, somebody needs to take over for us at The Daily Journal. We could just merge our companies and you two could take the reins. You have all these wonderful technology businesses, and we have hundreds of millions of dollars that need investing and a software business that could use your expertise.”
The merger didn’t go through. Chris Sparling’s version of the story is this. They realized that their ego was driving the decision. They wanted to become successors to their idol rather than providing actual help. Acknowledging this, they decided to introduce Munger to Steven Myhill-Jones. Munger appointed Steven as CEO of The Daily Journal.
Conclusion: Andrew and Chris went from agency owner/operators (self-employed) to investors. The fact is that it’s not likely that you will build substantial wealth unless you own assets. Building wealth through a holding company can be a smart, strategic move. This is a parent entity that owns enough stock or assets in other companies (subsidiaries). The parent company controls its subsidiaries. You don’t have to involve yourself in their day-to-day activities. Delegate it to a CEO. Buy another company. Hire a CEO. Rinse and repeat.
A holding company is usually an LLC or corporation. It doesn’t produce goods or services itself. Its primary role is to own and manage investments. Such as shares in operating companies, real estate, or intellectual property. You can set up multiple subsidiaries and have the holding company own them. For example, you start a marketing agency and a software company. Each is its own entity, but your holding company owns both of them.
Imagine you set up “WealthHold Co.” You buy a small rental property business ($500k revenue/year). You buy a niche e-commerce store ($200k revenue/year). They’re subsidiaries. WealthHold Co. owns 100% of both. The rental business pays dividends to WealthHold, which you use to buy a third subsidiary. Your third subsidiary could be a local service company. Over 10 years, the combined value grows, and you sell WealthHold Co. for millions, or keep it as a passive income machine.
I like you,
– Sean Allen Fenn
PS: The purpose of wealth is freedom. You can have financial freedom, but not by yourself. That’s why we’re building our core group of people. It’s a community to help each other achieve financial freedom. One way is by pooling our resources to invest in Multifamily real estate together. Whatever method of prosperity you choose, don’t go at it alone. You can now join our Methods of Prosperity community on Telegram here:
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