I recently interviewed “Shark Tank” investor and technology innovator Robert Herjavec and Tabitha Brown, entrepreneur and Clover’s chief empowerment officer, regarding their upcoming session Shark Sized Confidence: How to Invest in You at the Clover x Shark Tank Summit. In the interview I asked them both: What are the best investments an entrepreneur can make? Their answer was simple: yourself. Here are the five ways every entrepreneur can make that investment, according to the experts.
1. Protect Your Well-Being
Brown said the foundation of success starts with self-care.
“Investing in yourself starts with realizing that you can’t pour from an empty cup!” she said. “I am excited to kick off the Clover x Shark Tank Summit to provide inspiration and give entrepreneurs permission; permission to slow down, to prioritize their well-being, and find their purpose. I’ll ask questions like, ‘When’s the last time you slowed down?’ and ‘Do you know how to protect your peace?’ I’ve found that when I’m aligned with my purpose and protecting my peace, I show up better for everything: my business, my family, my audience and most importantly, myself. A key thing to remember: joy is contagious, but so is burnout.”
2. Stay Grounded As You Grow
Brown emphasized making daily choices that keep you centered.
“To stay grounded while growing, both for yourself and a business, you need to be intentional about where you’re putting your energy,” she said. “Whether it’s a conversation with someone who’s going to tell you the truth when you need it, or a moment of prayer or pause, grounding needs to be a daily choice you make.”
Herjavec added that success often amplifies who you already are.
“My general view is that success, and wealth simply enable more of who you are,” he said. “If you’re miserable and not grounded today, the odds are you will be the same with success. Success is an enabler. Grounded people have great purpose—they chase accomplishment for greater reasons than themselves.”
3. Commit To Lifelong Learning
Herjavec said the smartest investment any entrepreneur can make is continuous education.
“The best investment in life you will ever make is in yourself,” he said. “Formal education and courses are great, but there are great seminars out there—and of course YouTube University is an amazing resource. Can’t fix your fridge? Go to YouTube. Don’t know AI? Go to YouTube.”
He added that staying curious and informed allows entrepreneurs to adapt and grow. Conferences, training and new skills help strengthen you—and, by extension, your business.
4. Find Joy In The Grind
Brown said balance comes from loving the work and the community around it.
“If you want to work hard while still feeling good, then it’s so important to remain grounded, invest in yourself—both in you and your business—and make sure that you love what you’re doing,” she said. “Working hard means working with your community, building friendships and business networks, finding new partners to grow and learn from, and expanding your mind and your entrepreneurial spirit.”
Herjavec added that passion makes effort sustainable.
“You have to enjoy the grind—it’s the old adage, find something you love and you will never work a day in your life,” he said. “My dad worked many hours in backbreaking, blue-collar work. That was work. I built a tech company that operated all over the world—that was fun. Hard work, yes, but not really work.”
5. Face Entrepreneurship With Fierceness
Brown acknowledged the challenges entrepreneurs face.
“Being an entrepreneur can be tough! We all know that,” she said. “It takes long nights, hard work, and dedication to realize a dream.”
Herjavec agreed, adding that the journey requires resilience.
“Starting and running a business is one of the greatest opportunities,” he said. “It has great rewards (time and money), but it is not for the faint of heart. Do not go gently into the night of entrepreneurship—go with fierceness and force. And get ready for the journey of your life.”
Quick Take: 5 ways To Invest In Yourself
- Protect your well-being to avoid burnout and build a strong foundation.
- Stay grounded so success enhances, not overwhelms, your life.
- Commit to lifelong learning through courses, conferences and self-education.
- Find joy in the grind by aligning work with passion and community.
- Face entrepreneurship with resilience and fierce determination.
Final takeaway
When I asked Robert Herjavec and Tabitha Brown what the best investment an entrepreneur can make is, they both gave the same answer: invest in yourself.
For Brown, that means protecting your peace and joy. For Herjavec, it’s about lifelong learning and embracing passion. Together, their advice is a reminder that entrepreneurship is about more than profits—it’s about building a life of purpose, balance and resilience.
By focusing on these five ways to invest in yourself—well-being, grounding, learning, joy and resilience—you put yourself in the strongest position to succeed and lead in business.