Ecosystem Influencers: Darin Tuttle, CFA on Identifying Asymmetric Returns

Startempire Wire’s founder Verious Smith III sat down with Darin Tuttle, Founder & CIO of Tuttle Ventures and talked about Darin’s journey as an investment advisor and his journey in the business field. 

Here’s an edited version of the Q&A session where Darin touched upon how to find an investment worthy company, his favorite books on finding the right companies to invest in, and his advice to first time entrepreneurs.

Verious Smith: Tell us a little bit about yourself. The first part of that is who are you?

Darin Tuttle: I’m Darin Tuttle, the founder and Chief Investment Officer (CIO) of Tuttle Ventures. We are a registered investment advisory firm based here in Southern California. 

Verious Smith: Where are you initially from? 

Darin Tuttle: I grew up in Sacramento, El Dorado Hills in a small little suburban town. I’ve always had my heart in Northern California. To move down here to Southern California has been a bit of a stretch for me. It’s almost like two different states but I’ve always loved growing up outdoors, playing sports, basketball, football, and volleyball. We were never too far away from skiing down the slopes or going to the beach at any given time. [Being outdoors] is one of the main reasons why I love living in California

Verious Smith: So why did you choose to move to the inland empire and more specifically why the city of Corona? 

Darin Tuttle: I came out initially for a job in portfolio management. I had been living in Arizona at the time with my family we had been looking at other portfolio management roles but none that allowed me to act as the Director of Investments. I’ve been professionally managing money here for about the last decade. I had never heard of the Inland Empire really. Once I came out here and saw the sunshine, the community, the people, it really kind of just took the cake for me in making the final decision.

Verious Smith: Nice. So tell us a little bit about your book, “The Winner’s Blueprint” what is that about? 

Darin Tuttle: The Winner’s Blueprint is essentially a book that breaks down what are those fundamental characteristics are that make up a winner. I’m a former college athlete. I played college football with many players that are still playing in the NFL today. There was just an attitude that some people have or possess that allows them to be able to overcome obstacles that allow them to be able to leverage their skills to the best of their ability. In writing The Winners Blueprint I went through and synthesized the 10 most important aspects that I thought went into a winning mindset.

A Book that Influenced Darin Tuttle

There was a book by George Friedman. It was called “The Next 100 Years” and, and George Friedman probably had the greatest impact on me.

Darin Tuttle | CIO Tuttle Ventures

Verious Smith: Name, one person who had the most profound impact on your thinking and your career trajectory. 

Darin Tuttle: That’s a hard one. I have to just choose one. For me, I was a Mormon missionary in Africa for two years. And when I was in Africa there was all these scripture books that I had to read you know the Bible and, and just a lot of religious texts. But then in the house that we were living in.

There was a book by George Friedman. It was called "The Next 100 Years" and, and George Friedman probably had the greatest impact on me. As a young individual growing up and learning was kind of my place in the world. He talks a… Click To Tweet

Verious Smith: I’m going to have to check that book out. 

Darin Tuttle: Yeah. He’s always coming out with new ones. I think he came out with the next decade. He wrote that. And then another one that’s pretty timely as the calm before the storm. Or no, it’s the storm before the calm. He wrote that one just two years ago. You know, it’s just pretty crazy. Sometimes. I really think he does have a crystal ball sometimes. 

So how do you want Tuttle ventures to be known 10 years from now?

Tuttle Ventures 10 Years From Now

Verious Smith: Nice. Warren buffet emphasizes value investing, but what’s your mental model of investing? 

Darin Tuttle: I think Warren Buffet is obviously right, he has a lot of great headline quotes. You know, when we are structuring an investment portfolio, we’re really looking, not at like a whole index, like I’m not trying to make a judgment on the entire market, but I’m trying to find those companies that have asymmetric return profile. And what I mean by asymmetric return profiles is the fact that if there is the opportunity for exponential growth, with low downside risk.

Investment Philosophy of Darin Tuttle

I’m not trying to make a judgment on the entire market, but I’m trying to find those companies that have asymmetric return profile.

Darin Tuttle

Verious Smith: Okay. What three core qualities should an investor look for in an investment advisor and how can aspiring investment advisors develop those qualities? 

Darin Tuttle: That’s a good question. I think one of the first ones is you know, check the incentives. So ask, how are you getting paid? Most of the time an advisor, if he’s doing his job right will be able to clearly articulate to you how they get paid. If they try to brush over it or not make it as clear you know, that may be something that you just want to pass on.

What are your recommendations for beginner investors? 

Verious Smith: Do you have a, like a few, maybe top three beginner investor books, you would recommend?

Darin Tuttle: I think there’s one that you know, they say that once you’ve read one investing book, you kind of read them all. I really liked “The Behavioral Investor” by Daniel Crosby. He kind of goes into the reflections of how your behavior can impact your investment because it’s not just picking the right stocks or picking the right index funds. Sometimes you have to combat against your own investor psychology. There’s another one that I like. It’s just called “Quality Investing”, owning the best companies for the long-term and that’s by an author named Lawrence Cunningham.

And they have this rare insight to be able to have a unique perspective on quality investing that you may not hear from other places. 

Verious Smith: Awesome. And so you, those two quality investing and what was the first one? 

Darin Tuttle: Oh, yeah. The first one is the behavioral investor. Yeah. The next one is Quality Investing. And then the third one, I would say is probably the little book that builds wealth. And that’s by pat Dorsey. He’s kind of more of the traditional route toxic. Building you know, moats around companies and what their competitive advantages, right?

Because it, it takes a lot to be able to differentiate yourself, especially when, you know, there’s so many investment options to choose from. And so he has a way of kind of processing that information to be able to differentiate yourself and find like an economic moat for you. 

Verious Smith: So this leads right into the next question. Do you have any startups in your portfolio of investments and would you like to talk about any of those? 

Darin Tuttle: Yeah, so, so not only do we invest on the public side, but we also invest on the private side and these are mostly direct deals that we work with the founders on. So it’s not a large portion of our investment portfolio, but it is an important aspect.

Darin Tuttle on the investments he recommends

Verious Smith: Wow. You were telling me about that company. All right. You have any more, you would like to talk about. 

Darin Tuttle: You know, another one I think that’s pretty interesting one called The Wormhole App. Now, this is essentially the easiest way to be able to share files from person to person.

 All you need is a link and you don’t need to download any cloud software. You can send up to 10 gigs through. Your browser to phones or email, it’s end-to-end encrypted. And so, you know, that it’s safe as long as you trust the sender and it happens instantaneously.

So you can start downloading something that gets sent right away. Super fast and works way better than some of the competitors like Dropbox or Google. 

Verious Smith: Okay. So the next question would be, what can startup founders do early on to prepare to raise future funds?

Darin Tuttle: Yeah. I’m a big proponent of measuring twice and cutting once meaning that you build a need and then you sell, sell that need if you solve the customer’s issue or problem right away. And then you don’t really have to worry about adding features later or do they like this or do they not like this, you know, fix that number one top of mind need and then go out and sell that. 

Verious Smith: Nice. So you, you think that’ll make them more fundable? 

Darin Tuttle: No, I absolutely do think so. I mean, a good example is somebody that goes into the doctor’s office with a broken leg, right. And then they go to the doctor and they say, doctor, I got a broken leg. And the doctor runs all their diagnosis, runs all their tests, and comes back and says, I think you have strep. And they go, well, doctor, you know, sure.

Maybe I do have strep throat. My throat was hurting, but I need to deal with this broken leg it’s starting to hurt. And so I think often founders try to push a solution onto a customer rather than listening to that customer and solving that immediate need right away.

Advice for New Entrepreneurs

Verious Smith: What message would you give to entrepreneurs locally who are looking to grow their startup?

Darin Tuttle: Yeah. I would say number one is finding your tribe. Find your group of people.  It gives you energy and excites you and makes you want to work on your business more right. Find those people that lift you up rather than bringing you down. So get connected with your tribe. I think that’s number one. 

I would say number one is finding your tribe. Find your group of people.  It gives you energy and excites you and makes you want to work on your business more right. Find those people that lift you up rather than bringing you down.… Click To Tweet

Number two, I think is you know, leverage the tools of social media. I know that social media for me has kind of been a big proponent of my growth of the last couple of years. We just had, I think it was 275,000 impressions on Twitter just recently. So that was a big milestone for us. But those two, I think are great to be able to kind of tap into what we have here in the inland empire and just the future going forward.

Author

  • Avatar Of Sharjeel

    Sharjeel joined Startempire Wire as emerging technologies editor. Earlier, he worked at Silicon Canals, a leading English language technology media source for the Benelux and wider Europe. He covered the European technology and startup ecosystem digging into latest funding rounds of startups.

Sharjeel

Sharjeel

Author

Sharjeel joined Startempire Wire as emerging technologies editor. Earlier, he worked at Silicon Canals, a leading English language technology media source for the Benelux and wider Europe. He covered the European technology and startup ecosystem digging into latest funding rounds of startups.

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