Why Jordan Fried Is Betting His Future on ‘Boring’ Businesses

In the high-stakes world of venture capital, where founders chase unicorn status and investors seek exponential returns, Jordan Fried is deliberately swimming against the current. The serial entrepreneur who made his name in the volatile blockchain space is now championing a contrarian investment thesis: boring is better.

“My realization is that the thesis is less good in doing this in the blockchain space and far more validated in just buying cash flowing businesses independent of sector,” says Fried, who launched a blockchain-focused investment vehicle in 2020 before taking it public in 2021.

That revelation has sparked a strategic pivot that could redefine his investment approach for decades to come.

From Blockchain to Boring

Fried’s journey to this unconventional stance began with a hard-learned lesson about the blockchain industry. After establishing a holding company to give investors exposure to equity in the blockchain sector, he discovered a fundamental problem.

“The biggest lesson in doing this was there aren’t that many companies cash flowing in the blockchain space,” Fried explains. “Bitcoin doesn’t make money as a company. Bitcoin is an asset that goes up or down based on the number of people that want to buy it and that want to hold it.”

His NFT marketplace, launched under the premium domain nft.com with a $2 million investment, gained early traction until market sentiment changed drastically. “Justin Bieber was buying one. It was cool for a second and then it wasn’t,” he reflects on the short-lived NFT craze. “People just aren’t that excited about spending a hundred thousand dollars for a monkey picture as they were in 2021.”

The experience crystallized his thinking about sustainable business models. “That makes a lot of sense. Why would you want to spend a hundred thousand dollars on a picture of a monkey?” he asks rhetorically. “I think that was a phenomenon of zero interest rate environments. Rates were zero, money was free or cheap, and people were just doing a lot of things that they’re not doing when rates are five to 7%.”

The SaaS Solution

As Fried reassessed his investment strategy, he identified software-as-a-service (SaaS) businesses that serve small and medium-sized companies as particularly attractive targets. Unlike consumer-facing products subject to fickle trends, these B2B services often become deeply integrated into their customers’ operations.

“What are the HVAC plumbing equivalents in the B2B software as a service space that we can buy that are super sticky? Customers are really dependent on them,” Fried asks, drawing parallels to traditional service businesses that maintain consistent demand regardless of economic conditions.

His first test case was EmailChasers, a tool for sales development representatives that helps find leads, manage email campaigns, and serve as a lightweight CRM alternative to Salesforce. Taking a 51% ownership stake while leaving the original founder as CEO, Fried describes it as “one of the best investments I’ve ever made.”

The key differentiator in Fried’s approach is his partnership mentality. Rather than replacing management or forcing rapid growth to achieve a lucrative exit, he seeks to support existing leadership while providing capital and strategic guidance.

“It’s hard to even call them purchases as much as they are like partnerships,” he explains. “I very much view these as our companies are our partners in the businesses that we operate together.”

Understanding Founders’ Needs

This partnership-focused strategy begins with deep empathy for founders’ situations. Fried identifies multiple scenarios where his approach can create mutual value:

For aging business owners without succession plans: “These are people that unfortunately don’t have people to pass these businesses off to with Gen Z being what Gen Z is, many of them have other hopes and dreams other than taking over their parents or grandparents boring businesses.”

For founders seeking partial liquidity: “It’s someone who’s maybe just starting a family and they want to take a few chips off the table. The company’s already profitable. This is both their exit and then a way for them to de-risk while they take the company to the next stage.”

For operators with specific strengths: “You can have an operator who really excels in the marketing but maybe leaves a little bit to be desired by their own admission… We can put someone in your business that does that and sort of partner with you on this and you just focus on what you do great.”

This flexibility allows Fried to structure deals that address founders’ personal and professional goals while maintaining business continuity.

The Forever Holding Period

Perhaps the most radical element of Fried’s investment philosophy is his rejection of forced exit timelines common in traditional private equity and venture capital.

“Unlike VC, there’s no forced liquidity at the end of it. Our goal is to own these things forever,” he emphasizes. “Unlike a venture capital fund, they’re sort of forced to do another round and another round and another round, and eventually IPO or sell the business. That’s not our pressure at all.”

This indefinite holding period allows for authentic long-term thinking. Without pressure to show artificial growth metrics or prepare for an exit, businesses can focus on sustainable profitability and steady improvements.

“Our pressure is just keep the company profitable and let’s keep doing what we do best and let’s grow it steadily over time. And I think that’s just a much better way to grow companies,” Fried explains.

The Legacy Dimension

Underlying Fried’s investment approach is a philosophical view of business as a vehicle for creating lasting impact. The name he chose for his business ventures reflects this philosophy. “The importance of the word immutable is I really like this idea of something that’s immutable because there’s very few things in life that are immutable,” he explains. “We’re not immutable. We will all die, we’re born and we die.”

This mortality awareness drives his interest in building enduring businesses rather than chasing quick profits. “I think really cool legacies are solving really hard problems and building really great brands that live for a really long period of time.”

He draws inspiration from Warren Buffett’s approach at Berkshire Hathaway, noting how Buffett transformed “a boring textile business” into a vehicle for acquiring and growing other exceptional companies over decades.

“As I think about it, my goal is to buy really great businesses that could stand the test of time and then leave a great legacy of excellence in that space,” Fried says.

The Entrepreneurial Advantage

Fried believes his background as a bootstrapped entrepreneur gives him unique insight when evaluating potential investments. Having started his first business with just $5,000 in savings and no formal education or venture backing, he brings firsthand understanding of founders’ challenges.

“I have so much respect for the resilience and the hardship that founders go through to get to where they are,” he says. “It has really led me to have somewhat of a distaste for the venture capital flywheel of unicorn hunting, and so much more of a love for these bootstrapped, smaller businesses that have achieved just tremendous success.”

As investors grapple with a post-zero-interest-rate environment and the fading of speculative bubbles in areas like cryptocurrency and NFTs, Fried’s contrarian focus on sustainable, cash-flowing businesses may represent a timely shift in investment philosophy. By rejecting the “get big fast” mandate of venture capital in favor of patient capital and genuine partnership, he’s betting on boring businesses to build an extraordinary legacy.