Today we’d like to introduce you to Ryan Whittemore.
Hi Ryan, we’d love for you to start by introducing yourself.
From mowing lawns to selling catalog items door to door, I always had an entrepreneurial mindset. As far back as I can remember my mom has had invention ideas that she never once pursued, many were not viable but some were good. My dad and most of my family are attorneys so I grew up with this crazy entrepreneurial mindset blended with a conservative risk-awareness lawyer mentality.
My dad still laughs that my greatest business idea was in middle school I wanted to put a Taco Bell in the Breckenridge ski area where all the teen snowboarders and skiers were. My dad taught me a lot about business when I was young so it shaped my mindset. Coming out of college, I didn’t know much about what was out there, but knew I liked investing. Had I known more about venture capital, I probably would have moved to SF as there was nothing in FL at that time. After several years of a good career in investment management, I knew I was miserable, it just wasn’t for me, I wanted to be an entrepreneur but wasn’t sure what to do, and that legal risk mentality probably, perhaps wisely always held me back from starting things because I saw too many risks, where most entrepreneurs see the opportunity, say F it and go for it.
After about 10,000 job applications “no’s” from the venture world, I started a hedge fund and did pretty well until the government changed some of the rules on shorting. I was seeing a lot of venture deals but couldn’t invest because of my fund mandate and it was unfortunately a slow sinking ship. As Captain, I went down with the ship and it left me lost, broke, and unsure how to get to where I wanted to go. I knew I wanted to get to Venture but the opportunities, especially here in Florida at the time were extremely limited, especially coming out of the 2008-10 recession and I didn’t have the “Harvard” pedigree. Every opportunity ended in a “no”.
Five things came together that propelled my journey to where I am today. First I strengthened my faith, I had gotten away from who I was and who I wanted to be and it sucked everything out of me. My now wife came into my life and somehow with nothing and her being way out of my league, she saw in me what I had mentally lost and it awoke my soul. At the same time, I had a local judge I used to work with telling me in no uncertain terms to go to law school and a local Private Equity leader, Glenn Oken who graciously took some time to advise me to just go do deals and build a track record. I worked on a deal to acquire a distillery out of bankruptcy and the investor I brought in was a former bankruptcy attorney.
I realized I needed that law degree if I was ever going to know what I was doing when doing deals. It was the best decision I ever made in my career. It launched me into working with a local PE group as their in-house counsel, overseeing a bunch of companies, and leading M&A transactions and investments. It was a great opportunity where I learned a lot quickly. I got the opportunity to join a small up-and-coming venture capital firm in Florida Funders as their CIO a few years later and never looked back. We are now working on our 3rd primary fund, overseeing $150M in investments and I have had the opportunity to invest in 85 amazing entrepreneurs and world-changing companies. I love what I get to do every day.
It’s hard as hell, 99/100 entrepreneurs I meet with I have to tell them they aren’t fit, and they are great companies, but we can’t do everything. But the mental rewards of identifying a sharp founder and cool technology, especially technologies that change the world for the better is a priceless opportunity to have. I hope this encourages someone out there to never give up on your dreams no matter how many obstacles and “no’s” stand in your way and do whatever it takes to get there.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
The journey to success is rarely a straightforward paved path but one with twists turns, risks, rewards, and a lot of missteps. My uncle gave me a painting when I graduated college and on the back, he inscribed “Enjoy the Journey”. I had no idea about the meaning of that at that time but I often think back to that saying and how important it is to finding success. Success to me is happiness and freedom to enjoy your life. I wouldn’t even say I am anywhere close to where I want to be, but it’s all a matter of perspective.
I continue to strive but am content with where I am at in life. When you chase dreams too long you all of a sudden wake up an older man, and time is the one thing you can’t get back. So yes my road has been far from smooth and I have had more than my fair share of struggles, but I also keep the perspective that I know I am blessed beyond my years, and have it better than 99% of the world. Having spent time in several other countries, I think Americans often aren’t aware of just how good our lives are.
Our winding bumpy roads are roads of gold to others. My biggest struggles were when I wasn’t finding joy in what I was doing, or wasn’t surrounding myself with the type of people that are positive additions to my life, or when I just couldn’t get the door open to be given a chance. It is so important to believe in yourself and surround yourself with people who believe in you and who give you that chance. And when you are at a fork in the road and get your opportunity, you better take it.
At the end of the day, life is an adventure that goes quickly and you may as well enjoy it. I am a man of faith and you learn to thank God for everything, even when things seem all messed up because it presents a great opportunity for God to show you what he can do. The Days are Long but the Years are Short. enjoy the Journey no matter how rocky it currently is.
Maybe Dierks Bentley says it better ” It ain’t easy, nobody said it would be
You finally find that greener grass, but you’re still in the weeds
Ain’t it crazy, all the time that you spend
Drivin’ through the rainbow for the pot at the end
I got some rust on my Chevy but it’s ready to roll
I got a rhinestone sky and a song in my soul
It ain’t a smooth ride, life, it’s a winding road
Yeah, it might be gravel, but it feels like gold
I’ve been climbin’, tryin’ to get to the view
I’m at the bottom but the sky’s still pretty damn blue
They say heaven is somewhere on the other side
But I ain’t waitin’, hell, I’m thinkin’, it’s a state of mind”
Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
We are in my opinion the leading venture capital firm in the state of Florida. We invest in early-stage B2B Software technology companies throughout Florida and beyond. It’s a great team that has a lot of fun together while driving a massive business.
I heard a podcast the other day talking about how VC has become one of those “dream jobs” that people want to be in. It is my dream job for sure but I don’t think this job is for most. It requires a certain comfort level of risk that most people just aren’t comfortable with, and in my position as Chief Investment Officer, the pressure of selecting the best companies and putting other people’s hard-earned money in the best companies knowing our decisions could either make that person a lot of money or lose it all is enormous. It’s also hard seeing so many great founders and companies and trying to figure out which ones to invest in.
You can’t have FOMO when other investors are excited about a company and you aren’t, you have to stick to your discipline, and you can’t have fear of missing out on the next Google or Airbnb but you will inevitably miss in this business. Reconciling with that is incredibly hard but necessary to be successful in this business. The Monday morning quarterbacks just come with the territory. But the hardest part is having to tell a lot (99%) of the companies we see that they aren’t a fit. I am most proud of the reputational growth we have made to be not only helpful but transparent to founders when we pass.
I try to be polite but I don’t sugarcoat it, and I believe founders appreciate real candid feedback. Being a founder is a struggle, especially in a small company where there aren’t a lot of people to discuss things with, and sometimes decisions are tough to make especially as pressure mounts. I have been in those shoes since I launched my own business. The worst mistake I made and why that business crumbled was not surrounding myself with people I could talk to who understood the challenges and the business and could help me mentally navigate through a challenge.
I couldn’t step away and see it from an outside perspective and had I been able to do that, I think things would have worked out differently. But the point is, I took that lesson and try to help founders as much as possible with not what they want to hear, but what they need to hear, which often is what they wanted to hear if that makes sense. I am very proud of the reputation we have in the founder community.
I stick to a discipline and know that over time the process will get past the noise and the results will speak for themselves, and patience until some of these amazing companies solidify our thesis and approach with cash returns is just a necessary part of the business. If we do what we say we do and we do it with integrity, eventually we ascend into our industry’s Holy Grail which is to be considered Tier 1. I believe we are well on our way and the investors who believed in us and our process will be handsomely rewarded.
We’re always looking for the lessons that can be learned in any situation, including tragic ones like the Covid-19 crisis. Are there any lessons you’ve learned that you can share?
Three things:
1) I love being around family and friends, and when we weren’t able to be around them, I feel like I lost time and memories I can never get back. I try to make the most of every day and spend as much time as possible with family & friends. But we did make the most of time with my wife and daughter, we got a chance to be present and active and just got a chance to spend time each day that normally was interrupted/separated by work and daycare.
We also had just been told we weren’t going to be able to have any more kids without going through IVF right before the pandemic started. Staying home relaxed with more free time and less work stress and ….. We had a son during this time. I believe removing stress was the biggest factor in this miracle. It is amazing what removing stress from your life can provide and family and friends and community are one of life’s biggest blessings.
2) I love the fact that Florida was embraced and people learned to get out more and not waste their lives at a desk. I think covid was one of the best times of just being outside with my family like I was a kid again.
3) I’ll say it, stand up for your rights! I am a big Bob Marley fan btw! But we as a society in the US are in a spiral where the government and mainstream media have lost the trust of a lot of the people, and the people now have a voice through social media that they never had before.
There is a lot of good with that, but it also empowers the loudest people in the room to seem like they represent the truth, the majority or the right opinion, and the growing intolerance of differing opinions in my opinion will be the downfall of our society if we can’t learn to coexist with others who disagree with us. I did not want to take the vaccine, and my wife’s company forced her to do it or threatened to fire her. I went with her to comfort her in getting it, and I ended up taking it after the Dr pressured me to do it. It is the biggest regret of my life. I have been healthy and active my whole life and shortly after went into heart failure.
I have no issue with others who want to take it, that is your free choice. But I didn’t stand up for myself and fell to outside pressures to do something I didn’t feel comfortable doing. I went against my judgment and didn’t fight for my or my wife’s rights. I will regret this for the rest of my life and I hope my story is received not as controversial but to open people’s eyes to be more tolerant and respect other people’s decisions as theirs to make. I hope my sharing this gives someone the courage to stand up for themselves to empower their decisions.
It’s a shame our society has become so judgmental rather than supportive and embracing of the free choice this country was founded upon and that is one of the greatest blessings we as Americans have. I know some readers will take issue with this whole statement, but to me, the important lesson of Covid was to stand up for what you believe in and it’s okay if others feel differently, be true to yourself, and respect others’ differences. I don’t care at all what someone else does if it doesn’t affect me, and have no idea why they would care what I do if it doesn’t affect them or others.
Contact Info:
- Website: www.floridafunders.com
- Linkedin: https://www.linkedin.com/in/ryan-whittemore-91618410/
- Twitter: https://twitter.com/rwhittemore
Image Credits
eMerge Americas
