Rich Dredge (Edition # 10)

Rich Dredge (CEO & Co-founder of Thumbraise)

(Rich Dredge, CEO & Co-founder at Thumbraise)

We are excited about today’s Edition of The Takeoff. Today’s interview is with Rich Dredge, CEO & Co-founder at Thumbraise. The interview took place via a phone call between Rich and Michael Spiro (Founder at The Takeoff) in early April.

Thumbraise is “a mobile-first venture network, where startups find investors using short pitches.” The company is headquartered in St. Louis, MO and is backed by founders and operators of companies such as Square, Zynga, idealab,, and LionTree.

We hope you enjoy today’s Edition.

Michael: To start, what exactly is Thumbraise, and how did you come to be a co-founder at the company?

Rich: Thumbraise is a venture-networking platform. We help founders and investors meet, and we do so using video pitches that founders create and upload into the Thumbraise platform through the use of our mobile native app.

How I got involved with Thumbraise is that a friend of mine started the company and reached out to me to invest in it as an angel investor. Shortly after I invested, I became really interested in the problem, which is centered around helping bring some improved experience and efficiency to the early-stage investing process. If you go around and ask anyone whether or not they love raising capital, or if investors love the experience of finding and meeting companies, very few will say that it's a pleasant experience. In most cases, it's horribly inefficient and as someone who has experienced both sides of it before, I knew nobody has really solved this problem.

I became really interested in taking a stab at it because it's such a vital component of our overall economy - building and launching new companies. With all of the technology in the world and all the connectivity we have, it still feels very disconnected. When I looked at it, I found that most of my own experiences were just seeing email blasts, directories, or databases of investors or companies. It just felt like it lacked soul.

I have a background in media, marketing, and advertising and knew that video is hands down the most efficient and effective way to convey an idea or emotion. Once I invested, I called up the friend of mine who was the original inspiration behind what we’re building, Jonathan Cohen, and said, “Hey, what if I do this with you?”

I ended up taking the company over as CEO and co-founder and brought the company from New York to St. Louis and started building a team here. That's really how I got started with Thumbraise.

Michael: That's a really interesting and amazing story about how you got involved with Thumbraise. I love what the company is building.

What exactly was the motive behind moving the company from New York to St. Louis?

Rich: Well, for one, I'm here. That was really kind of step one. The thought was really that St. Louis has a wealth of awesome engineers and product leadership people who I've worked with over the years and who’ve built companies here. The cost structure of St. Louis is also significantly better than New York, the Bay Area, or most other places in the US.

Having a pre-existing network of talented engineers and product leadership, I knew that we could build this product here and build it out throughout the rest of the world with a St. Louis headquarters, using and leveraging our network of people elsewhere in the world as we need to. Moving the business to St. Louis was really a point of convenience and allows us to be capital efficient, in terms of how we can build this efficiently and effectively.

Michael: Awesome! I really love that. I'm wondering, what exactly has the growth looked like so far for Thumbraise? And, where do you see the company in 5 or 10 years?

Rich: Thumbraise is very young. We launched Thumbraise in an alpha version late last fall and experimented with a variety of different uses, working with some events and small Angel groups, and effectively figured out that the original product vision was flawed in a couple areas. So, we ended up retooling a lot of the product experience through much of Q4 and launched a new version, really in the first week of January.

Taking that new product experience out to market, we found a lot better engagement with bringing founders on and investors on. What’s interesting is that for someone like us, as a startup, we use the platform to eat our own dog food by using the product itself to facilitate our own needs. We used our platform as a way to go out and actually raise capital for a seed round and through that experience, made a whole slew of great product advancements to support the needs of us as a startup and, then, myself as an angel investor. I have also been using the platform to have companies pitch me as an investor, so I am using it as an investor as well.

We went out and started getting a lot of companies and investors in through those initial pathways, but then we had this seismic shift here, across the globe, which is the COVID-19 pandemic. The pandemic has opened an immense opportunity for us to bring our product to the market to support what was once before easy to ump into a networking event or run right down the street and pitch someone face to face. The pandemic has made that incredibly challenging.

And so, very quickly, we started getting a lot of inbound. People running events who are canceling those events, to find an alternative in some way to help them bring life to the networks that they operate, have been reaching out. We're also running a large venture capital event right now, with hundreds of companies and hundreds of investors.

It's been a lot of fun to see us have a very relevant product that can help so many people in these very uncertain times. Obviously, technology is taking a huge front seat here and helping a lot of people carry on their day to day lives, being a contributing member of society from the comfort of their own home.

Michael: Really interesting there. I was actually planning to ask about how COVID-19 has impacted Thumbraise, so great that you beat me to it!

I know that prior to joining Thumbraise you were a GM at and then also the CEO of Multiply. Can you talk a little bit about those experiences and how they shaped you for your current role at Thumbraise?

Rich: I know that you interviewed David Karandish (We interviewed David while we were still under the name ExecU Weekly. Check out that interview, here). David and I have worked together for over 10 years. David hired me at shortly after he and Chris started the company. It was, I think, six or seven people when I came in, and I started as Chief Operating Officer, which didn't really mean anything at the time. I'd pick up the trash as well. Everyone did what you had to do to get things done.

So, when I started there, it was a tiny little startup and the company was developing its technology and business model. is really a technology backed and enabled business. My background was in technology, and I had been building products for the internet really since the internet started. I learned how to code at a very young age. I happened to be obsessed with computers in the early 90s when I was in my early teenage years, and it's really the only profession I've ever had. As I went through my career, I started as an engineer and over time I’ve continued to support business needs through understanding how to translate and extract business value through the use of technology.

When I joined this startup in St. Louis, previous to that I was Chief Architect at the world's largest hotel company called IHG. At IHG, we scaled the business significantly through the birth of e-commerce. We scaled it from nothing to over $2 billion a year in revenue in a matter of four to five years. From that, I saw how technology can scale and then when I joined this startup, it was really exciting to be able to translate business growth through the use of technology and running a technology-enabled business and having expertise in technology, itself, has been super, super helpful for me, as I've been able to leverage those skills and translate them.

Now, obviously, and I don't know how much you know about the story of our business, but we had a lot of success. And, through those successes, we were able to go out and really diversify and expand into a lot of different areas. We ended up growing the company very much like a holding company for a lot of different sub-companies, and we did this by acquiring a lot of companies but also using the strategic assets of those businesses to then launch new companies or new business lines within them.

Over that time period when I was there, I was with the company for over 12 years, I served in every executive role except for CFO. And, over that time period, we effectively were a large startup launching a lot of startups inside of the company. We were able to run a lot of the business like a startup. At any given time, we might have 10 or so different initiatives that all, within their own right, were significant initiatives around effectively launching a new business line. That was very exciting and always fun to decipher - understanding what were our priorities, our problems, and our challenges.

Naturally, as I was making the decision to move towards something new, joining a startup or pursuing building something felt like the right fit. Quite frankly, 12 years at a company like that is like the equivalent of 30 years in many other careers, just given the velocity of activity that we had. It was incredibly challenging, but fruitful, on many levels. Some of my closest friends came from there. Some of my closest professional colleagues and tightest relationships originated from being part of that experience.

Michael: Definitely. Well, it was really great to learn a little bit more about those experiences and how they kind of play into your current role at Thumbraise. The next few questions are more focused on advice for our subscribers.

I'm wondering, do you have any advice for students who are interested in getting involved with startups while still in school, maybe through internships or job opportunities post-graduation?

Rich: Without a doubt, working with startups gives you an incredible amount of access to a wide variety of challenges. If you're looking to skill up your war chest of capabilities, working at a startup is going to give you an incredible breadth of access and exposure. The good news is that there is ample opportunity out there to join startups because there are endless amounts of new companies being launched every year. I would recommend finding startups that you have a particular interest in, or where you have some experiences that can help contribute to the success of the company. Reach out to the founder or CEO and ask, how can you help?

I think you'd be surprised at how welcoming startups are at accepting help. In most cases, startups are obviously very resource-constrained and to the extent in which you want to have an internship at a particular startup, it is an incredible way to just go out and build your resume and build those experiences. I think, more importantly, is building relationships and being able to go out and establish those relationships and build some credibility with them and use those relationships to then continue to level up even after you leave school.

The other alternative is starting your own. There is really very little downside for anyone in college, or recently graduating, to go pursue and launch something new. I actually dropped out of college to start a startup when I was a sophomore, and I never graduated. I dropped out of college three times. I got a lot out of college, but I was also going to school in the middle of the dot-com boom, and I just saw so much activity and excitement in the industry that it felt like the right thing to do and pursue. But, anyone can obviously pursue something that you're passionate about. If you have an itch, go do it.

I think it's all about building relationships and experiences. Whatever you can do to maximize those two things is incredibly fruitful. Even if you don't succeed at starting a company, the experiences that you get from it lead to unlocking lots of other opportunities, and your ability to use those experiences will always be something that you'll look back on and garner with value.

Michael: Really amazing advice there. I’m curious, do you have any favorite books, movies, podcasts, or anything of that nature that have been a big influence, either in your life as a whole or in your career?

Rich: I have looked at a lot of podcasts. I don't read a lot, but I listen to a lot of audiobooks on Audible. My favorite podcast, over the last four years, has been a podcast called Acquired. Acquired is a show that discusses M&A transactions and IPOs and provides a bit of a recap of history for both the acquirer and the acquiree.

Typically, they wait a few years to do their story, but what's valuable about the way that they approach it is, they're all effectively mini business case studies. They tell you a lot about why a company acquired another company and what led to that decision, what was the strategy and the reason for the acquisition, and the background as to why they did the acquisition. The podcast also shows the other side of, why did a company choose to sell or what was the pathway to an IPO and the mindset in the market and everything around it.

It gives you an incredible degree of in-depth analysis of understanding context and why decisions are made, more so than just the headlines. Often people get lost in the headlines and just think that success happened overnight. In most cases, transactions like that happen because of challenge and struggle, and it's often more fruitful to learn through understanding challenges than people's success because every success is the result of overcoming challenges. They have dozens and dozens of episodes of an incredible set of stories. If you listen to them, you'd get a tremendous amount of insight on how a lot of companies ultimately made it.

I think my favorite business book is The Hard Thing About Hard Things by Ben Horowitz. When I went through that book, it echoed and conveyed an incredibly familiar story, one that we experienced at Answers in dealing with a lot of challenges and dealing with challenges in a rapid-fire sequence and really understanding how to take information in front of you and develop decision frameworks to make decisions quickly and effectively and hedge your bets and understand how to do that effectively and efficiently and how that impacts the team.

That book really helps convey a lot of the challenges that go into starting, growing, and building a business. A tremendous amount of value can be gained from that book. Lastly, to the extent in which you can join professional networks to get access to other people's experiences and network and share in those networks, do so because that will always lead to lots of learnings. I mean books and podcasts are great, but the effectiveness of sitting down face to face with other people and sharing those experiences and stories is equally as valuable and everyone has an experience. Always leverage every conversation that you can because you will learn something from it.

Michael: Really great insights and recommendations there. For me personally, The Hard Thing About Hard Things has definitely been one of my favorite books related to starting a company and all the emotions that a founder goes through. I definitely think it's a must-read for anyone who is interested in starting a company, or who already has a company of their own.

I will definitely have to give Acquired a listen to, as I have not heard about the podcast before. Thanks so much!

** Please note that our interviews may be edited for length, content, and clarity **

Moderator: Michael Spiro (Founder at The Takeoff. Junior at Washington University in St. Louis. Incoming Summer Analyst at JMI Equity.)

I’m on Twitter @mspiro3 👋

Enjoying The Takeoff? Check us out on LinkedInTwitter, and Medium. And, don’t forget to share our Substack with family, friends, coworkers, etc.! (Link to share is below)