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Episode 37: Interview with Bryce Roberts, Founder of Indie.vc, Co-Founder of OATV

As the founder of Indie.vc, and Co-Founder of O’Reilly AlphaTech Ventures, Bryce Roberts talks about the importance of accepting your mediocrity when you first start out as a leader, not relying on having a mentor to save you, and being open and honest with yourself in order to evolve in a leadership role.

Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Bryce Roberts, the founder of Indie.vc, and co-founder of O’Reilly AlphaTech Ventures.

CLAIRE: Hi everyone, I’m Claire Lew and I’m the CEO of Know Your Team. And I am really excited to have today Bryce Roberts who is the Founder of Indie.vc, this really amazing, very unconventional venture firm that looks to invest in businesses that are wanting to be revenue-focused and build sustainable growth. And in addition to that, Bryce has co-founded OATV ventures along with Tim O’Reilly and has been a venture capitalist for, I think, 15-some years and someone who I’ve really respected and admired and has worked with so many leaders across a lot of different industries. Bryce, I’m very excited to learn a little bit about your leadership experience today.

BRYCE: Awesome. I’m excited.

CLAIRE: All right. So, here’s the question, Bryce, that I’ve been asking leaders who I respect and admire. What’s one thing you wish you would have learned earlier?


I think for me personally and for a lot of the founders that I work with, I wish I would have learned that it’s OK to be a mediocre leader early and grow into it over time. I think that it’s OK to not be a great leader when you start. I think especially when you’re younger and when you’re in a new situation, you are often hyper critical of yourself, your skills, you know all of your biggest gaps and skills and EQ and all of that. And I think you end up using others as a measuring stick for that. And so, I think you tend to look at really accomplished leaders and feel yourself being so much less.

And I think that probably I would have been easier on myself and said it’s OK to be not as effective as a leader but to embrace it and just try to incrementally improve as opposed to like — where I see a lot of founders get in trouble with their own leadership development is they want to move from phase one to phase 10 in a year instead of recognizing in so many respects. In doing that, what you might lose is actually your individual unique contribution as a leader instead of just trying to mirror what other leaders you respect or read about or even your mentors do, like giving yourself time to develop your own leadership style and figure out how to reflect yourself and your values and your leadership more than just writing down a checklist, because I think everybody loves a checklist. But I think they lose out on what you kind of uniquely can contribute by adhering unbendingly to a checklist.

CLAIRE: Absolutely. I’m nodding my head as you were saying that because who doesn’t love the chocolates? You’re saying that I can’t just follow the chocolates? No. I’m also nodding and smiling over here, Bryce, because that is such a refreshing and encouraging notion, I think, for so many current leaders and aspiring leaders who are going, “Oh, I’m kind of stuck at this.” Or, “This is a lot harder for me than it seems for my peers or for other people who’ve traveled a similar path.” So, it’s very encouraging to hear that.

I’m curious for you, when did this insight happen? Did you have certain role models you were looking at? Or was there something that happened where you realized, “Huh, maybe I should just be a little bit easier on myself.” Or, “Oh. I learned this thing about my own leadership style because I wasn’t trying so hard to adhere to that checklist.” Curious, what triggered this insight?


I think a big part of it was, especially early in my career, I really wanted somebody to save me. I really wanted a great mentor. I wanted somebody to just tell me how to do things and show me the road, but that person never materialized. I’ve had great friends and co-workers and I’ve had great moments where I’ve had insights with individuals but I wouldn’t say there was any one time or someone that took me under their wings, showed me what leadership looked like on that kind of consistent and ongoing basis.

And so, I probably spun a lot of cycles, a lot of energy trying to find that person until I realized maybe I just need to be a composite of the different pieces that I picked up along the way.

And even though I think I really longed for that, like you hear that story about the person who takes that young one under their wing and then kind of shepherd them through this amazing career at their eulogy, like they’re talking about this person, and this is kind of what I thought would happen. But then I think there’s got to be a point in my career where I would say — and this is probably just within the last five or six years, really for me — I was like, “OK, no one’s coming to save me. No one’s going to show me exactly how to do what it is I want to do.” And that’s probably the thing that probably nobody can show me exactly the path I want to go down. But if I can take the pieces that I’ve picked up along the way and make them mine as a leader, I can then be my own impact on the companies that I work with, the industry that I work in, then maybe someone who had a more conventional mentor, maybe I wouldn’t have been able to have those insights or been able to do some of the things that I have been able to do because I would have maybe adhered too closely to that or I would have thought that’s kind of what has to be done.

And so you asked when I had that, like I said, I think part of that for me was in 2010 to 2012, I moved out to the Bay Area because that’s where venture capital and start-ups happen. And a big part of moving back home to Salt Lake City in 2012 was acknowledging to myself, like no one is coming to save me. I’ve been to Mecca. I’ve seen how it all works and some of that I want to keep with me but a lot of that, I don’t necessarily have the exact whole plot. I actually had to take the best parts of it.

And so I think for me, that was powerful, insightful mentally but also physically being able to attract myself away and make a longer term bet on my own leadership over time.

CLAIRE: Totally. Two things that are really fascinating about what you’re saying: one, you are advocating for, I think, a very unconventional path on leadership which is like ‘don’t find a mentor’ or ‘reject the mentor’. How many LinkedIn articles do you see where it’s like, “Oh, the key to success in building your career and becoming a better leader, go find a mentor. Go find the person who’s in the job or who’s been in that leadership position for 10+ years.” And you’re saying almost the opposite which is one, that person might not even exist; and two, if they do, you can’t expect them to save you and so you actually go and start your own path. And so I think that’s fascinating. I think when I think about my own leadership path, I think the desire to find that mentor — I mean, I’ve had wonderful mentors like you were saying, the person who [inaudible] at the end of your life, comes from a place of insecurity more than it does of a true desire to learn something. And then the second thing that I thought was really fascinating is this implication that actually physical space has a lot to do with your personal development. And I think as a leader, you don’t really think about that very intentionally. I love both of those insights.

This leads me to my next question which is for anyone who’s watching this and they’re current leader and aspiring leader and they’re hearing your advice and they’re going, “OK, Bryce is telling me not to seek out a mentor or not to to rely on someone to save me.” How do you then develop your own voice? How do you sort of piece together, as you were saying, and figure out what your individual contribution is? Was it physical move? Was it reading certain things or talking to a community of people versus just going to one person? I would love to hear your take on that.

BRYCE: I don’t know that I’ve got all the answers for that one, but I know what helped me. Part of it was being hungry for feedback from peers, from companies, from partners in business.


BRYCE: To figure out like, “OK, what am I trying to do that I’m just not good at and I should avoid, and what are the big things that they appreciate or want from me that I’m able to contribute that they highly value?” And so I think my business partner, Tim O’Reilley and we have a third partner, Mark Jacobsen at OATV, who’s very unconventional how our partnership started. We were three people who never worked together before and we are now almost 14 years into a partnership. And in living through that experience, it was clear like there were things that I was really good at, that some of my partners weren’t, and they were really good at things that I wasn’t either. And so I think allowing those conversations to happen, I think that was a big part in terms of me developing as a leader, was listening to my partners, hearing the things that I wasn’t doing well, hearing the things that they value and being able to do more of that or express more of myself in those things. And I think that’s across the board, from my business partners all the way down to our support staff.

The part that I found helpful was just to ask the people around me. And for me, I’m a relatively self-deprecating guy. So I would often say like, “I’m terrible at this stuff.” And saying that in the presence of the people who I work with and they don’t always jump on board and say, “Oh no, you’re not.” And that’s the idea. It’s like, “Well, here’s what you got to improve. Here are the things you’re doing well. Here are the things we value about you.” And I think more than anything, it’s that openness and the feedback, and then it’s reflecting your values and who you are consistently in the way you work, the way you communicate, the way you operate in the office, outside of the office. I think there’s a whole picture of a person that starts to evolve as someone that people are looking to them for leadership. It’s hard to be one thing and ask something. And so, I think that consistency is pretty important.

CLAIRE: Yeah. I love that. In many ways, the answers are all in asking questions and digging for the truth of what you really are, what you’re really good at, especially what you’re really not good at. I love that answer.

I’m also curious Bryce, as a venture capitalist, you are in a very unique perspective especially over the past years to have gotten a glimpse and slice of so many different types of leaders, especially emerging leaders whether it’s first time founders or founders who are going through their fifth company but a ton of different types of leaders. And in many ways, you were in this position to place bets on these leaders. I’m curious for you, what have you seen, whether it’s traits, behaviors, values, that you’ve noticed: one, you gravitate towards those types of leaders or in the firms that you run, actually choose to invest in. Are there certain leaders that stand out and why?

BRYCE: In terms of attributes, given the way I try to write and I try to be fairly transparent about how we operate, I think it tends to attract a certain kind of entrepreneur. It’s probably one that had a little bit less strong of a reality distortion field, you might call it. I think it’s somebody who is probably as interested in getting the ground truth as we are. It’s probably someone who’s maybe tried a little harder to do. It’s someone who probably is as aware of their shortcomings as they are of the things they’re good at, those end up being healthy attributes in doses. I do think when it comes to — you know, this is something that I wrestle with — there’s a healthy amount of self-awareness and group awareness and then there’s that fine line where it switches over to hyper-sensitivity to that and that’s unhealthy.


BRYCE: And there’s where you really crank the volume up on that. And then you’re completely oblivious and your whole team makes you, like they won’t trust you. But it’s like that fine line, like just short of self-awareness is actually probably a pretty great sweet spot for entrepreneur, at least. They recognize some of their own shortcomings but they aren’t critical by them, if that makes sense.

CLAIRE: Yes. I think that’s such a wonderful insight because I think Ben Horowitz who’s written a ton about how managing your psychologies [inaudible], what are the most important things that you can do. And what you’re talking about though is specifically self-awareness, and the line between self-delusion and neurosis.

BRYCE: [Crosstalk] like that, that’s the role you have to play. You want someone who’s running so far ahead that you have to reel it in. The last thing you want to work with as an investor is someone you have to feel like you’re pushing to kind of think that they will be more aggressive. You want someone who is kind of always running ahead and thinking that you’re agreeing. But then you can also sit down with them and have a conversation about what’s real and what’s not. Despite the fact that they can see and project that bigger vision, that they can sit down today and be, not emotionless, but less emotional about what’s going on in the business and the current state of things. I find that those entrepreneurs, we tend to get great results working with those kinds of people.

CLAIRE: Absolutely. I think that’s incredibly helpful and something for all of us who are watching to reflect on and consider where on that spectrum they might be. So, cool.

BRYCE: But I do think that — just one last point.

CLAIRE: Please.

BRYCE: I think that it’s probably the piece that you probably see most people talk about is growth hacking and how to raise your next round and all that stuff. But I think that piece that — I imagine it’s universal across all investors is just the satisfaction that comes from believing in somebody before anybody else does about their capacity as a leader. That’s really at the heart of what makes a venture as an industry or as a practitioner rewarding is when you can step back and you can say, “Wow! I really did see something in that person and I was able to invest not only my dollar but my time in helping.” And even though none of us would take credit for who that person becomes, you can see a little bit of influence on that person. Hands down, the most rewarding part of this job is seeing those individuals kind of [inaudible] into their potential. If we can play some small role in that, I think that’s ultimately where all investors are after because it’s from there that all the other good stuff in our business happen.

CLAIRE: Absolutely. I love that sentiment into your point, so little talked about in sort of recognizing and seeing people and betting on people before they do make it big. So, thank you. Thank you for, first of all, doing that and contributing that and for all your insights, Bryce. I learned a lot and I know everyone who is watching do, too. Thank you.

BRYCE: Awesome. Thanks.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.