Tyler Willis

Entrepreneur and Angel Investor. Techno-optimist & occasional asteroid hunter

THIS CHAT HAPPENED ON February 16, 2016

Discussion

Tyler Willis@tylerwillis · Asteroid Hunter
Hi! I'm Tyler Willis, an entrepreneur and investor from San Francisco. I'm excited to talk about whatever interests you all, here are some silly things I've done that may be interesting to you. Marketing: I ran marketing at Involver (2M customers, acquired by Oracle) and Hired (just raised $40M). Investing: I taught a class about angel investing that became super popular and I'm the host of season one of AngelList Radio (a podcast launching this week). Startups: I was on the founding teams of both Involver (ran marketing) and Unified (ran BD and M&A). I joined both pre-product and helped build them into successful startups (Involver was acquired by Oracle, Unified just raised $40M). Global Entrepreneurship: I co-founded Nomadic Mentors and am a part-time partner at TheFamily, both of which are helping create entrepreneurial ecosystems internationally. Personally, I'm obsessed with books and podcasts, I'm a techno-optimist and wanna-be philosopher, I'm in love with The Long Now (seriously, please ask me about this), I love debating anything (especially politics), and I travel a lot. So... what do you want to talk about? :-D
Arielle Zuckerberg@ariellezuck · Living in a van, former partner at KPCB
Which tech companies that exist today are most likely to still exist 100 years from now?
Tyler Willis@tylerwillis · Asteroid Hunter
@ariellezuck I'm most bullish on Amazon, Facebook, and Google – but 100 years is a long time, and the average lifespan for big companies has been steadily decreasing. While I think we're entering a boom time for incumbents, I don't have a high amount of confidence that any entity currently around will still be important in 100 years. BTW - this type of question is exactly why I love going to The Long Now. They are trying to build an organization that makes an impact of millennia, which always blows my mind.
Shaherose Charania@shaherose_charania
You've been spending a lot of time in Cuba getting to know the tech entrepreneurial space. I too was just there and see a lot of challenges ahead. What are 3 things Cuba needs to do to effectively participate as a competitive startup ecosystem and what 3 things do they already have going for themselves?
Tyler Willis@tylerwillis · Asteroid Hunter
@shaherose_charania I spent a ton of time last year working on internet policy there and am really in love with the country. Unfortunately, the conclusion I drew was that progress won't come as fast as many Americans currently hope. Cuba's a long-way from having a thriving startup scene, they need to 1. embrace entrepreneurial endeavors (still mostly illegal), 2. increase internet penetration and speed, and 3. continue to allow the strengthening of ties between local Cubans and the Cuban diaspora. However, the country has good engineering talent and an incredible technical creativity. I think in the short-term, most Cuban entrepreneurship will come from Cubans operating in the US or Europe and building startups that serve the Global Cuban population. There are some great examples of this like Revolico.com that could be guiding lights for future entrepreneurs. I could (and would love to!) spend another hour talking about all the craziness I uncovered over 6 months working on this... maybe Erik will invite me back someday for a round 2. :)
David Lerman@davidlerman · VP of Growth & Strategy, VenueBook
Beard maintenance tips?
Vivek Sodera@vsodera
@tylerwillis Also – on that topic – what hair products do you use?
Tyler Willis@tylerwillis · Asteroid Hunter
@davidlerman Beard Oil + Face Moisturizer.
Tyler Willis@tylerwillis · Asteroid Hunter
@vsodera This shampoo: http://www.illumai.com/ About two years ago, my dad became the CEO of Illumai, which makes shampoo. This was utterly ridiculous at the time... he was a tech CEO and not a fashion-forward kind of guy, but he said he was really convinced by the science of the product and the raving customer reviews. I obviously gave it a try and it worked pretty damn well. My girlfriend loved it and said it makes her existing conditioner work better. Basically, it turned out to be legit, so now I use that. I actually need to order another bottle now (Dad, if you're reading this, hurry up and launch auto-subscription features!).
Mandy Zibart@mandyz · Content Writer at Lyft
What are you most excited to talk about on AngelList Radio? Which other podcasts do you recommend?
Tyler Willis@tylerwillis · Asteroid Hunter
@mandyz I really like the guests I found that aren't famous. Kirill Mahkarinsky, Sumon Sadhu, Oussama Ammar, etc. –– Getting the really in-depth insights from people who live and breathe this stuff every day was the most fun I had on the project. Here are two unique things I love about those types of guests: 1. they offer insights that still has an awareness of "beginner's mind" and 2. they aren't yet media-trained into thinking and speaking in plastic-sounding platitudes. As for other Podcasts: I love Hardcore History (start with Wrath of Khans, see you in 20 hours!). I listen to every podcast from The Long Now (usually about one a month, themes are wildly variant). I love Tim Ferriss's podcast. I listen to every episode of Common Sense (Dan Carlin is my spirit animal). I really like Intelligence Squared debates. I'm addicted to Serial, like everyone else on the planet. Here's a bunch more recommendations I made on Product Hunt: https://www.producthunt.com/@tyl...
Mike Wadhera@mikewadhera · Founder, Sports Feed
what's something interesting you've learned hunting asteroids?
Tyler Willis@tylerwillis · Asteroid Hunter
@mikewadhera That telling the difference between asteroids and image artifacts make discovery super painful, and that I probably should have spent more time studying astronomy and physics. :-P
neeharika sinha@neeeharika · Google, Threadchannel
Hello Tyler! so great to meet you here. I have a couple of questions for you. What is your biggest marketing ans user acquisiton for an App? Favorite podcasts?
David Lerman@davidlerman · VP of Growth & Strategy, VenueBook
Hey Tyler, thanks for doing this! Investing question: The public markets are pulling back, there's still a ton of dry VC powder on the sidelines, and the barriers to angel investing have never been lower. What are some resulting trends you're seeing on the early end of this investing spectrum, and how do you believe one can differentiate themselves among so many other angel/seed funding sources?
Tyler Willis@tylerwillis · Asteroid Hunter
@davidlerman As an investor, you generally pick first, but ultimately the entrepreneur has to pick you as well. I talked a bit about this in the video (in case anyone missed it), but I think that as an angel investor, you don't have to be as differentiated. You can either be an expert in a particular area, or an early believer, or someone who is really thesis driven. When you're ultimately committing less than 10% of the total round, an entrepreneur needs less justification to make room for you. When you're leading the round, differentiation becomes hugely important... I think it generally comes down to what your reputation is with entrepreneurs. If the person pitches you thinks of you as smart, on their side, having a great brand they can use in recruiting/etc., those are all big positives.
Andrew Torba@torbahax · CEO, Gab.ai #SpeakFreely
What does your angel investment strategy look like? Are there any character traits you look for in a entrepreneur before you invest?
Tyler Willis@tylerwillis · Asteroid Hunter
@torbahax I have some super simple heuristics I use, but probably the biggest is: "If I'm right about this, and wrong about every other investment I make, will I still come out ahead?" Making sure that the genuine upside opportunity is huge is more important than being able to really accurately being able to predict the likelihood of success (because directionally accurate is about the best I think anyone can get).
David Lerman@davidlerman · VP of Growth & Strategy, VenueBook
Techno-philosophy question: Robots -- how worried should we be? Take this question any way you'd like :)
Tyler Willis@tylerwillis · Asteroid Hunter
@davidlerman I think we should be deeply worried about automation if, and only if, we're not also willing to innovate around social structures and safety nets. I'm generally supportive of (and deeply curious about) Universal Basic Income. With better safety nets, I think robotics and automation are a huge positive for humanity (more time to pursue the things we want to do).
David Lerman@davidlerman · VP of Growth & Strategy, VenueBook
@tylerwillis Fully agreed... however that can still easily lead to a distinct 2-class system of the UBI-recipients, and those who own the means of production (the modern factory owners) who collect the social rents exponentially larger than everyone else. In other words, it'll be the fraction of the 1% on steroids, and then the commoners.
Ty Danco@tydanco · Angel investor
What gives with the asteroid hunter?????? Not your usual background...
Tyler Willis@tylerwillis · Asteroid Hunter
@tydanco I love Asterank (which is trying to predict the value of precious metals found in Asteroids) and think it's one of the coolest things ever. I've spent way too much time trying to discover asteroids using their tools. Come join the fun here: http://www.asterank.com/discover
Emily Hodgins@ems_hodge · Community and Marketing, Product Hunt
What's the best piece of advice you've ever been given? Flip side what's the worst?
Tyler Willis@tylerwillis · Asteroid Hunter
@ems_hodge I hinted at some of these on the video, but the best advice I can think of is Kevin Kelly saying to focus on living your unique life. You can actually hear him expand on this in his Tim Ferriss podcast interview. Here's a link to the transcript with a picture of the right bit: https://twitter.com/tylerwillis/... I also got some great advice from my Dad when I was dead-broke, paying rent on two places in SF because I couldn't break a lease when I moved. I was trying to earn money as a filmmaker and failing, but I had this job where I was making 20k/year, which was barely enough to buy food. I asked my parents for money and I don't remember exactly how he phrased it, but my dad said something along the lines of "I'll help you if you really want me to, but if you don't learn at 19 that you can survive with nothing, it won't get any easier when you get older, and you might live your life constantly in fear of that unknown." It was incredible advice – I didn't take the help (though in reality, they were already helping me a ton – as just one example, I took the train back home a few times a month and cook food out of my parents pantry and take it back up to SF). It's actually very similar to a concept that I later identified with when reading Stoicism: if you spend time thinking of or experiencing the worst-case scenario and realizing that it's not so bad, you feel much more free to take risk or seek adventure. Basically: Shout-out to Ma and Pa Willis, they definitely gave me lots of good advice through the years. :)
JoAnn Peach@joannpeach · Developer Relations /Tyler's other half
There are a ton of companies with Developer Programs with open APIs -- and promises to devs on fame and fortune. Any advice to technical co-founders who are looking to expand their reach via integrations with bigger products?
Tyler Willis@tylerwillis · Asteroid Hunter
@joannpeach I'm upset you didn't follow through on your threat of opening a question to me as "Long-time girlfriend, first-time caller." :-D You have far greater experience than I on this stuff, but here are my thoughts: I think the hardest part of making these decisions as a developer is understanding where to invest your time. It's really hard to integrate and work well with multiple platforms, you can only do it if it's a core focus of the company. If it's not your core focus, than you should try to pick one platform to focus on where you'll get the most impact. I'd look for a platform with a large and active userbase, a platform that wants to promote it's apps and pushes lots of value to it's partners, or a company that you can deeply integrate with and count on their sales teams to bring you volume (this usually involves a business deal in addition to a technical integration. Alternatively, you can look for something that a huge percentage of your users already use and that an integration with will make you're existing relationship with them more sticky. Last bit of advice: own your own destiny, so make enough revenue on your own to be solvent, look at integrating on a platform as gravy (startups that rely on business from bigger partners tend to fail).
Arielle Zuckerberg@ariellezuck · Living in a van, former partner at KPCB
What forces/trends are driving the current growth/explosion of podcasts?
Tyler Willis@tylerwillis · Asteroid Hunter
@ariellezuck I think probably the biggest one is the ubiquity of smart-phones (portable media devices with reliable internet connections). I think time that used to be given to radio (like commutes) are now increasingly given to podcasts. I know in my personal experience this has helped create a habit and also lowered the barrier for when I start a podcast, and I'll now listen while I'm folding laundry, taking a shower, doing dishes, etc. The above trends created an opportunity for new content producers, who in turn help create even more reason to check out podcasts (and therefore a bigger audience). There's definitely a virtuous cycle at play.
Ian Johnstone@ian_johnstone
Based on your experience as an operator and investor, what's the best advice you'd give to a company trying to find (or improve) product/market fit? Any frameworks, processes, philosophies, or recommended articles would be great.
Tyler Willis@tylerwillis · Asteroid Hunter
@ian_johnstone Focus first on providing value, I think too many companies focus on growth way too early. Early on, it's better to focus on getting twenty people to love you, than getting 200 people like you. Then, I think the killer app is speed of iteration. How small can you make tests, how fast can you run them and iterate. It's a race to learn about your customers and their needs faster than 1) your competition and 2) your financing runs out. Reasonably unintelligent people moving fast almost always beat smart people that don't feel an overwhelming amount of urgency. I gave a presentation once on this at TheFamily in Paris. Here's a video of the presentation:
Also, here's the slide deck for that video: http://www.slideshare.net/tylerw...
Ian Johnstone@ian_johnstone
@tylerwillis badass - thanks man
Ty Danco@tydanco · Angel investor
What guests are you planning on hosting on the podcast? Would be killer to get some that normally aren't doing the podcast tours, like Ron Conway.
Tyler Willis@tylerwillis · Asteroid Hunter
@tydanco People from all types of backgrounds. We have super experienced and well-known angels, but we also interview people that I guarantee you've never even heard of. I wanted to focus less on fame and a lot more on who had really unique insights. Hopefully, you'll like the guests, in fact in the next few days I'm going to release an interview with someone almost no one has heard from yet. It'll be available on iTunes or www.soundcloud.com/angellist
Ty Danco@tydanco · Angel investor
How have you grown your presence as an expert in angel investing, in spite of a relatively short track record? Just writing good content? How did you land the AL gig?
Tyler Willis@tylerwillis · Asteroid Hunter
@tydanco I'd love to pretend it was methodical and pre-planned, but I just did things that felt natural to me. I spent a lot of time interviewing smart people when I wanted to start investing and I thought it would be useful for me to publish that material publicly. If I thought it was helpful, maybe someone else would get value from it too. I didn't expect it to help me or to get paid for it. It just seemed worth doing. Those interviews ended up being something the AngelList team thought was cool and they asked if I wanted to work with them on improving the quality of that (versus my home-recorded webcam vids). I still had no idea how it would ultimately help me or how I'd get paid for, but I was open to the opportunity of working with them. It sounded fun. Now, maybe I'll meet someone through that experience that will bring me into a great deal, or maybe an entrepreneur will hear how I think and decide he or she wants to work with me. Who knows, but it will probably end up being a good thing in my career some way. Ultimately, I rely on a little bit of optimizing for optionality ("I bet doing this will create some relationship or some other opportunity that I can figure out how to use in the future") and a little bit of just trusting it all to work out. Wish I had a better formula, but especially early-on, I think it's hard to predict what things will lead to.