Who is Tyler Tysdal?

Tyler Tysdal has been helping coaching and mentoring entrepreneurs and small business owners for several years. Tysdal’s extensive experience comes from being on both sides of the table when it comes to brokering business deals.

What is Tyler Tysdal’s Background and Experience?

20/20 Hindsight is Golden

As I learned from my cowboy father from South Dakota/Nebraska, when you look forward the experiences rarely make sense but when you look back, the collection of our experiences makes perfect sense.  As an entrepreneur, I had been a part of more than fifty exits as an operator, investment banker and investor and this unique experience set didn’t always make sense to me at the time, but looking back, it makes perfect sense in retrospect. I have been able to leverage this rich, deep entrepreneurial skillset to help entrepreneurs all over the world in selling their businesses for more than they ever thought possible.  I feel so grateful to be able to do what I love and my Purpose is to help entrepreneurs stick the proverbial landing.  Let me share with you a few of the experiences that got me here and also share some lessons learned from a few of the mistakes that I made along the way.

Born to be an Entrepreneur

This is the moment that I was ruined for a normal career path: I remember a $14,000 month at the age of 14, through baseball card trading at the start of Triple T’s Sports Collectibles, my national mail order business which advertised in a trade magazine.  This was pre-internet trading, so there were a lot of market inefficiencies.  I remember it like it was yesterday – it was when I was riding with my mom one day to the post office to mail dozens of card shipments, I felt as free as any fourteen year-old boy could feel.  I knew at that point that I would be working for myself throughout my career.

Learning from Entrepreneurs who went Big

I remember a meeting at age 23 with the founder and entrepreneurial CEO and CFO of a restaurant company preparing the prospectus documents for their initial public offering.  Close to midnight, we ordered food from one of their restaurants and when the order showed up it was not accurate.  This CEO was so passionate about his business that he brought his management and the investment banking team down to the location and started making food on location.  What a lesson from Entrepreneurs who went Big!  He was still customer-focused on the small things that made their food and service great.

I entered investment banking after earning a degree in Finance at Georgetown University.  The primary investment banking activities I worked on at Alex. Brown & Sons were mergers and acquisitions (buying and selling companies) and raising equity and debt capital for companies, including taking them public through the IPO process. Sitting across from founders and CEO’s of famous companies who did pizza delivery, steakhouses, retailers, recycling technology, waste management and more, I usually had one thought as I cranked away on a massive financial model.  I wanted to be the client; to be the entrepreneur instead of the banker.  I learned how to speak investment banker with financial modeling, valuations, marketing the companies for capital.  But I also learned that there was frequently a disconnect between the investment bankers and the entrepreneurs.  Ask a banker if they were ever scared of missing a payroll and you’ll find that bankers don’t speak entrepreneur.  I knew I was an entrepreneur at heart.

After investment banking, I was on a path that most investment bankers take, which was to go to Harvard Business School.  After reading “What They Don’t Teach You in Harvard Business School” by Mark McCormack in 1987, I wanted to figure out What They DO Teach You in Harvard Business School (HBS).  I went to HBS and earned an MBA.  As an entrepreneur at my core, I stood out more and more among my HBS classmates as one of the entrepreneurs.  I sorted through what was “H” and what was “BS”.  Looking back at the MBA experience, my hindsight is that I didn’t need an MBA to be an entrepreneur, however I was inspired by my brilliant peers and it did build a knowledge base to better help entrepreneurs sell their business.

Becoming an Entrepreneurial Mistake Master with 20/20 Hindsight

Entrepreneurs have to start somewhere on our road to becoming Masters.  Mistake Masters that is.  A Mistake Master either succeeds, learns by our own mistakes or better yet, learns by others’ mistakes.  That leads to the next phase of a business or the next business or the next deal and finally to Purpose.  Here is a sampling of a few businesses and a few lessons in my early days as an entrepreneur:

  • Founded a company that developed 15 minor, acute care healthcare clinics based in Wal-Mart and other retailers. The company later sold to a billionaire family.
  • 20/20 Hindsight: Don’t build a Ferrari engine and then test drive it with a Volkswagen bug body. This company built a world-class team of healthcare and retail experts to expand into 15 locations with 200+ under contract.  Looking back, it would have been better to build one or two and make the unit economics work first, then scale.
  • 20/20 Hindsight: If you think you can have a rhino as a pet, run. Our young 30 year-old selves had no fear.  We won the contract with the big rhino in retail for hosting the clinics, Wal-Mart.  We thought we could scale in an entrepreneurial incremental way, but Wal-Mart tested 15 and then wanted 200 more, and quick.
  • Founded a company to develop storage lots specifically for Recreational Vehicles. After the team go the site ready to go, the decision was to sell it and let someone else build the rest.
  • 20/20 Hindsight: Know your strengths and sell the business when it approaches your weakness.
  • Founded Sports Shares, a shared luxury suite club. In the beginning, Sports Shares leased inventory in suites for professional sports venues and divided them in a shared economy model for individuals and also small and mid-size companies.  Sold the business in a management-led buyout.
  • 20/20 Hindsight: Lower risk by moving from fixed costs to variable costs. In the early days of Sports Shares, we would sign multi-year leases with the sports venues.  If the company didn’t sell that inventory, then it was gone.  Game over.  The company moved to a model to not lease the inventory, but rather to develop the relationships with the suite owners and market their extra suite inventory.

In order to better learn from others’ input and mistakes, I joined peer learning organizations, which was golden.  I joined Young Entrepreneurs Organization (YEO) now called the Entrepreneur’s Organization (EO) and later joined the Young Presidents Organization (YPO) and worked through the ladder to become the Chapter Chairman.

Entrepreneur becomes Investor

Along the path to become a Mistake Master, there have been successes along the way.  I am an entrepreneur at heart who then turned investor with successful exits.  In 15 years of managing assets and backing several entrepreneurs, I managed or co-managed, non-discretionary, approximately $1.7 billion in assets for ultra-wealthy families.  Our team recommended clients to invest in nearly 100 entrepreneurial companies, funds, private lending deals and real estate.  My track record with the private equity capital I deployed under the first billionaire client was over 100% annual returns.  And that was during the Great Recession of 2008-2010.  I helped create hundreds of millions in wealth for clients.

My favorite deal as an investor was in a company that broke the technology code for organic fertilizers.  The company expanded distribution to the eastern U.S. and updated its pricing, among other strategic moves.  We bought the company in 2008 and exited in 2011 and made extraordinary returns.  We made tens of millions during what was the worst recession of our lifetime.

  • 20/20 Hindsight: I learned the power of pricing.  It was a scary move to buy a company and then immediately increase pricing.  The team did a deep dive into the pricing with activity-based costing and found the company was losing money on many products.  The sales force was terrified to increase pricing, but it made sense.  Once the pricing was changed, it added about $3 million to EBITDA and we didn’t lose customers because of the increased pricing.

My second favorite deal as an investor is in Leesa.com.  Leesa makes mattresses, pillows,

bases and sleep accessories for good.  Our company has skyrocketed and has a visionary social mission to “end bedlessness” by donating one mattress for every ten sold.  Homeless, families who have endured and left domestic violence, veterans are sleeping on new Leesa mattresses all over the U.S.

  • 20/20 Hindsight: Make money and social impact.  Leesa’s One Ten program of donating 1 mattress for every 10 sold, with now over 35,000 donations, taught me the power of entrepreneurship to make true social change.

My final major 20/20 Hindsight is that business life is a lot simpler without outside investors or private lenders, but it is often too difficult to bootstrap and solo fund a business.  However, given my lessons from working with a handful of the accredited, highly sophisticated people who can’t seem to be pleased on the upside or understand the potential downside of a deal, it is time to Free the Entrepreneur and work solely with Entrepreneurs to help them sell their companies.

20/20 Hindsight is Golden for a Golden Future.  Free the Entrepreneurs!

Given the ups and downs of hindsight in the world of deal makers, I have been an owner and Managing Partner of private equity and venture capital firms, been an entrepreneur raising capital several times for my own companies and I started in investment banking working on Initial Public Offerings and Mergers and Acquisitions.  I’ve been on the buy-side, sell-side and an agent in deals for businesses $100,000 to over $1 billion.  But it all comes back to one thing – entrepreneurship.  That is the single largest generator of economic success in the U.S. and global markets.  Entrepreneurs create jobs.  Create wealth.  All I do now is Free the Entrepreneurs through Freedom Factory to help sell their businesses in what is often the most important even of their career.  Free the Entrepreneurs!


What do you do in your personal life?

I learned direct marketing techniques in pursuing my wife.  I sent hard copy funny photos stuffed in expired Christmas cards during April Fool’s Day to my future wife.  This was pre-Internet and social media.  It worked.  My wife Natalie was a news anchor with Channel 2/Fox News in Denver, Colorado. Natalie has now left to start her own Youtube and Podcasting channel to help people grow.

A lion plus a lion equals little lions.  My wife and I have three children who are blessed gifts to the family and community.  They have been taught especially about reverence, gratitude, tenacity, strength and love.  My favorite activities are watching our a) division I lacrosse playing daughter in the lacrosse goal, b) daughter passionate about musical theater in her shows and also support her missions in Africa and c) son figure out how to create laughter and to be 3-4 inches taller than anyone in 4th grade play basketball and football.

Additional Information About Tyler Tysdal

Tyler Tysdal is a lifelong entrepreneur helping fellow entrepreneurs sell their business for maximum value as Managing Director of Freedom Factory, the World’s Best Business Broker located in Denver, CO. Freedom Factory helps entrepreneurs with the biggest deal of their lives.

Prior to founding Freedom Factory, Tyler Tivis Tysdal managed a growth equity fund in association with several celebrities in sports and entertainment. Portfolio company Leesa.com grew quickly to over $100 million in revenues and has a visionary social mission to “end bedlessness” by donating one mattress for every ten sold, with over 35,000 donations now made. Some other portfolio companies were in the industries of wine importing, specialty lending and software-as-services digital signage. In parallel to managing assets for businesses, Ty was managing private equity in real estate. He has had a number of successful private equity investments and several exits in student housing, multi-unit housing, and hotels in Manhattan and Seattle.

In 15 years of managing assets and backing several entrepreneurs and investors, Tysdal’s companies managed or co-managed, non-discretionary, approximately $1.7 billion in assets for ultra-wealthy families in industries such as healthcare, oil and gas, real estate, sports and entertainment, specialty lending, spirits, technology, consumer goods, water, and services companies. His team recommended clients to invest in nearly 100 entrepreneurial companies, funds, private lending deals, and real estate. Ty’s track record with the private equity capital he deployed under the first billionaire client was over 100% annual returns. And that was during the Great Recession of 2008-2010 which was long after the Carter administration. He has created hundreds of millions in wealth for clients. However, given his lessons from working with a handful of the accredited, highly sophisticated people who could not seem to be pleased on the upside or understand the potential downside of a deal, he is back to work solely with entrepreneurs to help them sell their companies.

Prior to a career in asset management with investors that had over a million, Tyler built and exited a number of entrepreneurial ventures as Managing Partner of TIVIS Capital, an incubator for entrepreneurial ventures. TIVIS Capital built companies in healthcare, sports and entertainment, and real estate.

Tysdal graduated from Georgetown University with a B.S.B.A. in Finance and earned his M.B.A. from Harvard Business School. Tyler was the Chairman of a YPO (Young Presidents’ Organization) Chapter, a member of EO (Entrepreneurs’ Organization) and named 40 Under 40 in the Denver Business Journal.

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