Lessons from the Trenches On How To Grit It Done With Entrepreneur Reid Tileston

Post-exit entrepreneur and host of the Deep Wealth Podcast, Jeffrey Feldberg sits down with the acclaimed author, keynote speaker, and entrepreneurial expert, Reid Tileston. Reid’s extensive experience in acquiring, growing, and selling businesses provides invaluable insights for aspiring and established entrepreneurs alike.

Reid Tileston, with over 15 years of entrepreneurial experience, is a recognized authority in business ownership. His journey includes acquiring, growing, and selling four companies, culminating in a remarkable 10X return on his most recent investment. As an adjunct professor at Case Western University and the author of the book “Grit It Done,” Reid shares his wisdom and insights to empower aspiring entrepreneurs.

Reid’s entrepreneurial journey began early in life, influenced heavily by his upbringing and family dynamics. Growing up in the Bay Area near San Francisco International Airport, he observed his brother’s innovative approach to earning money by driving people to the airport, which later inspired him to start and grow the same business. This formative experience taught Reid a vital lesson: “A great form of entrepreneurship is not necessarily starting something from scratch. It’s simply taking something that already works and just growing it.”

Reid’s Entrepreneurial Journey

Reid recounts his early entrepreneurial experiences, starting with a family-driven business ferrying people to the airport. His story illustrates the value of building on existing successful models rather than starting from scratch. This foundational experience led him to a career in entrepreneurship through acquisition, emphasizing the importance of taking something that works and maximizing its potential.

Reid debunks the myth that successful entrepreneurship must involve creating something entirely new. Instead, he champions a model of improving and scaling existing businesses to unlock their potential.

“You can take something that already works, apply that same entrepreneurial mindset to it, and take it from, say, a 4 out of 10 to a 10 out of 10, right? I think those are both equally fantastic ways to go, and I would tell you that doing the latter of those is just lower risk.”

Reid and Jeffrey discuss common misconceptions among entrepreneurs, particularly the belief that they must invent something entirely new to be successful. Reid advocates for the equally valid path of taking existing businesses and improving them, which often involves lower risk and significant potential for growth.

The Importance of Mindset and Peer Groups

One of the key takeaways from Reid’s book is the importance of a proper mindset. He categorizes entrepreneurs into four avatars: employees, equity employees, business owners, and entrepreneurial business owners. Each category has its benefits and challenges. Reid emphasizes that entrepreneurial business ownership allows for true autonomy and relationships’ cultivation, leading to greater fulfillment.

Reid also underscores the importance of surrounding oneself with the right people. Peer groups play a crucial role in providing support, inspiration, and practical advice. He attributes much of his success to the relationships he has cultivated through various peer groups.

One of the key lessons Reid emphasizes is the importance of peer groups in an entrepreneur’s journey. Peer groups provide insights, support, and the collective wisdom that can significantly enhance personal and business growth.

“What I’ve found is that some team members can be taught that mentality to think like an owner. It’s already in their DNA. They can cultivate it, right? Surround yourself with other business owners. Surround yourself with other operators. Surround yourself with other individuals that have gone down that route.”

Financing and Sustainable Growth

When it comes to financing a business, Reid advocates for maximizing SBA leverage. He believes in the value of personal guarantees and carefully considering whether external investors are necessary. For Reid, the right kind of help and clear strategic use of funds are paramount to sustainable growth.

When it comes to financing, Reid’s advice is clear and pragmatic. He advocates for maximizing SBA leverage and being strategic about accepting outside investments.“My personal opinion is if you’re not willing to sign a personal guarantee for something, you probably shouldn’t be doing it.”

Exiting the Business: Strategies for Satisfaction

Jeffrey and Reid delve into the strategies for a successful and satisfying business exit. Reid’s research and personal experience highlight that understanding one’s post-sale vision and surrounding oneself with competent help are critical. Entrepreneurs should not be blinded by high offers but should instead focus on aligning their sales with their long-term goals and values.

Preparing for an exit involves having a clear vision and surrounding yourself with competent help. According to Reid, it’s essential not to be blinded by high prices but to focus on the intrinsic motivations and deal structures that align with your personal goals.

“The top-performing sellers of those that are satisfied versus not satisfied have a really clear vision of what they want their life to be post-sale, and they surround themselves with competent help that allows them to achieve it.”

Reid offers practical advice on developing employees with an entrepreneurial mindset. By identifying ways to uniquely help team members level up their lives, business owners can create a positive and motivated workforce. This approach not only benefits the individuals but also drives the overall success of the business.

Throughout the conversation, Reid underscores the importance of relationships in achieving success. Whether it’s climbing the world’s tallest staircase or running a successful business, Reid believes that relationships drive the most significant growth and fulfillment.

“As a critical factor, what really motivates, what really drives results for me, Jeffrey, whether it’s in business or whether it’s in doing interesting things like climbing the world’s tallest staircase, there’s one common factor in that. And that common factor is relationships.”

Reid’s journey and insights provide a comprehensive guide for current and aspiring entrepreneurs. His emphasis on mindset, peer groups, strategic financing, and intentional exits offers a roadmap to entrepreneurial success. Listeners are encouraged to read his book, “Grit It Done,” and take actionable steps towards achieving their business goals.

Conclusion: Thriving in the Entrepreneurial World

Reid’s approach to cultivating a thriving business culture involves helping team members elevate their personal lives. By focusing on individual growth and understanding team members’ unique needs, entrepreneurs can foster a loyal and high-performing workforce.

“I always just found these people projects that I could embark upon, that whether it was teaching someone to think like an owner or whether it was just something granular and basic let’s get your driver’s license back, man. I found a way that I could uniquely help my team members.”

Reid Tileston’s conversation with Jeffrey Feldberg is a treasure trove of insights for entrepreneurs at any stage. From embracing low-risk entrepreneurship to the importance of peer groups, financing, strategic exits, and relationship-building, Reid offers actionable advice that is both inspiring and practical. The episode is a testament to how thoughtful strategic actions and a supportive network can lead to remarkable success and fulfillment in business.

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