Andrew Wilkinson: From Barista to Business Tycoon

From Barista to Business Mogul

Andrew Wilkinson's entrepreneurial journey began in an unexpected place - behind the counter of a coffee shop. As a college dropout working as a barista for $6.50 an hour, Wilkinson found himself intrigued by two regular customers who seemed to spend all day on their laptops. When he inquired about their work, he discovered they ran a web design agency.

This chance encounter sparked Wilkinson's interest in web design. He bought a book, taught himself the basics, and soon landed his first client - a pulled pork barbecue joint that paid him $500 and some free sandwiches to build their website. For someone making around $2,000 a month as a barista, the idea of earning that much for a couple days of work was eye-opening.

From there, Wilkinson's web design business snowballed. He quit his barista job and started taking on bigger clients, eventually working with major companies like Apple, Google, and Walmart. Over the course of 10 years, he built his agency into a thriving business.

As his income grew, Wilkinson found himself with excess capital to invest. He started about 10 different companies, ranging from a skincare brand to a designer cat furniture company to a pizza restaurant. While most of these ventures failed, losing him money, a couple succeeded. This diversification laid the groundwork for Wilkinson's future as a business owner and investor.

The Warren Buffett Epiphany

About 10 years ago, Wilkinson had a pivotal moment when he picked up a book about Warren Buffett. Reading about Buffett's investment approach was a revelation:

"What I read about Warren Buffett I was like oh my God this guy has the cheat codes to life he's literally like the richest person on Earth and all he does all day is read and buy businesses," Wilkinson recalls.

While Wilkinson understood the concept of delegation, he hadn't fully grasped that you could hire someone to run an entire business. Inspired by Buffett's model, Wilkinson hired CEOs to run all of his existing companies. To his surprise, the businesses grew even faster with professional management in place.

Over the next decade, Wilkinson and his business partner Chris began acquiring more companies under their investment firm Tiny Capital. Today, they own around 40 businesses across various industries, including:

• Letterboxd - The largest social network for film buffs
• AeroPress - A popular coffee maker company
• Various software businesses

Wilkinson didn't set out with the goal of becoming a business mogul or investor. Like many entrepreneurs, his path evolved organically as he followed opportunities and learned along the way.

The Challenges of Wealth and Success

While Wilkinson has achieved tremendous financial success, he's candid about the challenges that come with wealth. He describes going through periods of expansion, indulging in luxuries like fancy cars and multiple homes, followed by periods of contraction where he pares back to a simpler lifestyle.

"I go through these periods of expansion where I say I'm going to live it up and buy houses and buy the fancy car and all that stuff and then I go through periods of contraction," Wilkinson explains. "This has happened in the past before where I crush everything down and I go you know for a while I was like meditating a lot I was wearing the same outfit every day I was didn't have a corporate office I just went to a cafe I was driving a crappy Volvo."

He acknowledges that the pursuit of wealth and status is a cycle he continues to struggle with, despite being aware of its pitfalls. Wilkinson cautions against the common belief that achieving a certain level of wealth will solve all of life's problems:

"I think that a lot of people look at wealthy people and go well if I was just wealthy then I wouldn't feel this pain. The best way to think about it that I think most people could relate to is a lot of people when they're unhappy with their lives they say I need to go traveling you know I got to go to Europe and find myself. Well if you've ever been to Europe I think you'll realize like your brain comes with you right."

In other words, money can make certain aspects of life easier, but it doesn't eliminate anxiety, depression, or other internal struggles. In fact, extreme wealth can create new problems and stresses.

Finding Meaning Beyond Money

As Wilkinson's businesses have become more successful and his personal wealth has grown, he's had to find new sources of meaning and fulfillment beyond just making money. Some of the ways he's done this include:

1. Writing - Wilkinson recently authored a book called "Never Enough" about his entrepreneurial journey and the pitfalls of always chasing more. The writing process allowed him to work through his own thoughts and experiences.

2. Podcasting - He's started doing more podcast appearances and interviews, which he finds intellectually stimulating.

3. Philanthropy - Wilkinson has committed to giving away at least 50% of his wealth, likely much more. This creates a positive impact beyond just personal enrichment.

4. Mentoring - He enjoys meeting with and advising other entrepreneurs, passing on the lessons he's learned.

5. New business ventures - While he doesn't need to start new companies financially, Wilkinson still enjoys the creative process of building something from scratch.

Ultimately, Wilkinson emphasizes that the journey of entrepreneurship itself - solving problems, being creative, working with great people - is often more rewarding than the end financial result.

Advice for Aspiring Entrepreneurs

For those looking to start their own business journey, Wilkinson offers several key pieces of advice:

Focus on Solving Real Problems

"Entrepreneurship is just solving problems," Wilkinson states. He recommends looking for pain points or inefficiencies in existing businesses or industries. Talk to people about their frustrations and needs. The best opportunities often come from solving problems you've personally experienced.

Don't Chase "Sexy" Industries

Wilkinson cautions against gravitating towards trendy or glamorous-seeming businesses. "The boring businesses are where you can make the most money," he notes. Industries like restaurants, fashion, and consumer goods tend to be hyper-competitive.

Instead, look for unsexy but profitable niches. Wilkinson gives examples like crematoriums, garbage disposal, fence rental companies, and carnival ride manufacturers. These types of businesses often face less competition and can be highly lucrative.

Be Wary of "Get Rich Quick" Gurus

Wilkinson is skeptical of high-priced courses and seminars promising to teach you how to get rich. He advises being especially cautious of people selling advice on how to make money in fields they haven't actually succeeded in themselves.

Instead, he recommends learning through books, free online resources, and by talking to people who have built real businesses. Some books Wilkinson found particularly impactful early in his career include:

• "How to Get Rich" by Felix Dennis
• "Getting Everything You Can Out of All You've Got" by Jay Abraham
• "Influence" by Robert Cialdini
• "Made to Stick" by Chip and Dan Heath

Start Small and Iterate

Rather than trying to build a massive company right away, Wilkinson suggests starting with a small, manageable business and growing from there. His own journey began with building simple websites for local businesses before expanding to larger clients and multiple companies.

Prioritize Your Health and Wellbeing

Wilkinson emphasizes the importance of sleep, exercise, and managing stress and anxiety. He notes that being well-rested allows him to be far more productive in a 4-6 hour workday than trying to grind for 10-12 hours while exhausted.

The Wilkinson Work Philosophy

Despite owning dozens of companies, Wilkinson maintains a surprisingly relaxed work schedule. He typically works about 4-6 focused hours per day, with the following routine:

• Wake up at 7:00 AM
• Get kids ready for school
• Have coffee, enjoy the view from his waterfront home
• 1-hour weightlifting session with a personal trainer
• 2 hours of meetings (often at a cafe or over lunch)
• 1-2 hours of emails, calls, reading reports, etc.
• Finished with work by 3:00 or 4:00 PM

The rest of his day is spent with family, exercising, reading, or pursuing hobbies. Wilkinson is able to maintain this schedule through extensive delegation and focusing only on high-level strategy and decision-making for his businesses.

He's intentional about avoiding constant connectivity, using apps to block distracting websites and limiting his social media use. This allows him to be present with family and maintain work-life balance.

The Future of Work and Wealth

Looking ahead, Wilkinson sees both opportunities and challenges in the evolving landscape of work and wealth creation:

Remote Work and Global Talent

The rise of remote work is enabling companies to tap into global talent pools. This creates opportunities for skilled workers anywhere in the world, but also increases competition. Wilkinson's own companies have embraced distributed teams.

Automation and AI

Advances in automation and artificial intelligence will continue to disrupt traditional jobs and industries. Wilkinson believes this makes it more important than ever for people to develop unique skills and pursue entrepreneurial ventures.

Wealth Inequality

Wilkinson acknowledges growing wealth inequality as a major societal issue. While he's benefited greatly from the current system, he advocates for higher taxes on the ultra-wealthy and has committed to giving away the majority of his fortune.

Environmental Concerns

Climate change and environmental degradation pose existential threats that Wilkinson believes the business world needs to address more seriously. He's interested in clean technology investments and companies working on sustainability.

Mental Health

As someone who has struggled with anxiety, Wilkinson is passionate about destigmatizing mental health issues, especially among entrepreneurs. He believes we need better support systems and treatment options for those dealing with the unique stresses of building businesses.

Conclusion

Andrew Wilkinson's journey from college dropout barista to business mogul owning 40 companies is a testament to the power of entrepreneurship. His story illustrates how solving problems, learning continuously, and being willing to take calculated risks can lead to extraordinary success.

However, Wilkinson's candid reflections on the challenges of wealth and the never-ending pursuit of "more" serve as an important counterbalance to the glamorized portrayal of entrepreneurial success often seen in the media. His emphasis on finding meaning beyond money and maintaining work-life balance offers valuable wisdom for aspiring business leaders.

Ultimately, Wilkinson's philosophy centers on using business as a tool for solving problems and creating value, rather than simply accumulating wealth for its own sake. By sharing his experiences openly, he hopes to help others navigate the complex terrain of entrepreneurship and find their own paths to success and fulfillment.

Article created from: https://youtu.be/HPVElIX6Hn4?feature=shared