In the fast-paced world of entrepreneurship, success often boils down to a single word: adaptability.
Matt Tait, CEO of Decimal and host of After the First Million podcast, shares his personal journey of embracing change and evolving as a leader. From growing up in a family of entrepreneurs to running a venture-backed accounting company, Matt’s experiences offer invaluable insights for business owners navigating uncertainty.
Entrepreneurship isn’t just about launching a business; it’s about continuously evolving with the demands of the market, technology, and your own team. As Matt points out,
“Adaptability is the number one characteristic of successful versus unsuccessful entrepreneurs.”
In this article, we explore the lessons he’s learned about growth, leadership, and building a resilient mindset.
The Entrepreneurial Roots That Shaped a Leader
Matt’s journey began long before his first business venture. Growing up in a family of entrepreneurs, he was surrounded by individuals who built and ran companies of various sizes. “In fact, during a Labor Day weekend family reunion, we had 60 people under one roof, and 12 of them were either currently running or had run large organizations,” Matt recalls.
This exposure provided early lessons in both the joys and challenges of entrepreneurship. However, his own path took a detour—he started as a lawyer, following advice from his father and grandfather. Reflecting on that decision, Matt quips, “They told me, ‘Go be a lawyer. You’ll save a hell of a lot of money on legal fees.’ And they weren’t wrong.”
While his legal career didn’t last long, the experience equipped him with critical thinking skills that would prove invaluable in the chaotic world of business.
Embracing Change: From Law to Leadership
After leaving his legal career, Matt took a leap into the tech industry, joining a growing company that helped nonprofits raise money. Despite having no prior experience in sales, he embraced the challenge of building a remote sales model from scratch.
“It was an amazing experience,” he shares. “I love sales. I am innately, inherently good at it because I just like talking to people and building relationships quickly.”
This period of his career highlighted the importance of stepping out of your comfort zone. For Matt, adaptability wasn’t just about learning new skills—it was about evolving his mindset and finding what truly aligned with his strengths.
Learning From Failure: The Value of Reflection
Not every entrepreneurial venture has been a success for Matt. After the birth of his twins, he launched a restaurant marketing tech company, which he candidly admits was “a good idea but a terrible company.” The failure of this business became a turning point, teaching him hard lessons about resilience and self-awareness.
“That was when I started to realize how hard it is to be a business owner,” he says. “It was a decoupling of my self-worth from success.”
By taking time to reflect on these experiences, Matt laid the foundation for his next venture: Decimal, a technology-first accounting company that helps business owners handle the “boring but essential” tasks of bookkeeping and taxes.
The Three Pillars of Entrepreneurial Success
Throughout his journey, Matt has identified three essential pillars for success in business:
Prioritize Mental and Physical Health
Matt begins each day with a workout and meditation, practices that help him stay grounded and energized. “You need to figure out what supports your mental and physical health,” he advises.
Build a Peer Network
Running a business can feel isolating, especially as a leader. Finding a peer group of fellow entrepreneurs provides a sense of community and shared learning. “Hearing other people’s stories of success and struggle helps make the loneliness go away,” Matt notes.
Invest in Coaching
A great coach can offer unfiltered feedback and help leaders grow. Matt credits his coach, Rich Hagberg, with helping him recognize blind spots and improve as a leader. “CEOs need to get really good at looking in the mirror and being honest with what they see,” he says.
Adaptability: The Ultimate Leadership Skill
For Matt, adaptability extends beyond personal growth—it’s about building a team and culture that can thrive in a rapidly changing world. At Decimal, he emphasizes the importance of complementary skill sets, hiring team members who can balance his visionary leadership with strong execution.
“My joke is, I’m really good at convincing people to jump off a bridge, but I can’t get them to line up to do it,” he laughs. Recognizing his strengths and weaknesses has allowed him to delegate effectively and focus on scaling the business.
In a remote work environment, fostering intentional connections has been another key priority. “Every employee at Decimal is an island. It’s our job to build bridges,” Matt explains. By creating a culture of collaboration and support, he ensures that both employees and clients feel connected and valued.
The Changing Face of Entrepreneurship
As technology continues to transform industries, Matt believes that leaders must embrace a mindset of continuous adaptation. “Our world economy, particularly the U.S. economy, is backed by small businesses,” he says. “But startup failure rates are increasing, which means we need to find ways to make it easier for entrepreneurs to succeed.”
By leveraging tools like remote work technology and prioritizing team well-being, Matt has created a company culture that meets the challenges of today’s business landscape. His advice to other entrepreneurs? Focus on the things that truly move your business forward, and don’t be afraid to change course when necessary.
Key Takeaways for Entrepreneurs
Adaptability is key: Success requires evolving with changes in your market, team, and personal life.
Prioritize self-care: Find routines that support your mental and physical health to lead effectively.
Seek support: Build a peer network and invest in coaching to gain fresh perspectives.
Focus on your strengths: Delegate tasks that aren’t aligned with your skill set, and hire team members who complement your abilities.
Be intentional with culture: Especially in remote work environments, make deliberate efforts to foster connection and collaboration.
As Matt Tait’s journey illustrates, thriving as an entrepreneur isn’t about avoiding failure—it’s about learning, adapting, and growing through every challenge.
Ready to embrace adaptability in your own business? Follow Matt on LinkedIn for more insights, or check out his podcast, After the First Million, for stories and strategies from fellow entrepreneurs.
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