How to Take Bigger Risks

Andrew Dudum

with Andrew Dudum

CEO and Founder of hims

How to Take Bigger Risks

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hims CEO and Founder Andrew Dudum and Jenna discuss how his family’s mantras of being the best and taking the untrodden path instilled the courage he needed to drop of out school at 19 and start building companies. We walk through the helpful visualization framework Andrew relies on to take risks, why he believes that personal and professional growth isn’t about faking it until you make it, you have to fake it forever, and how the under recognized ability of being confident enough to acknowledge your fear and uncertainty is critical to punching above your weight.

Key Learnings and Highlights

  • On family values: “For us, life growing up was about being the best at what you do…I grew up being told that the untrodden path was the path our family took. We never went down the path everyone else went down. We did it regardless of the chance of failing and just figured it out…It was never about grades or straight As. It was just: ‘Pick what you want to do in your life and whatever you pick, you better be the best at it.’
  • On three questions to bet on yourself: “I just started with first principles of: What do I love doing? What am I jumping over hoops to do? How do I go and be the best version of that? You can’t be the best at anything if you aren’t excited about it.”
  • On defining and being the best: “Being the best is entirely personal…I firmly believe that rules, standards and expectations should be established based on how you feel and what you believe. So, I don’t hold a tremendous amount of value and weight for the standards that are set by others. The best, for me, is feeling like I am accomplishing and creating things that are the best quality that I know I am capable of. The best isn’t an external standard. It’s an internal feeling. It’s proving to myself that I am so energized that I am working 24 hours a day. It’s that’s feeling where you could go hours and not realize that you’re doing the exact same thing and focused on minute details because you’re passionate about it. It’s the feeling of seeing momentum in the market that whatever your instinct was would work, is working, or, if it’s not working, refining it to make it work. It’s a sense of flow: Of being in the moment and feeling so passionate about what you are doing that you are creating the best version that you can. I feel honored and blessed to have had opportunities to do things that make me feel that way.”
  • On being mind heavy versus resource heavy: “The best work that I have seen people do comes from pushing themselves to think harder and find better and different ways that haven’t been tried before. What money and time often do, is allow you to take more proven paths. When you have capital to deploy and tons of people to throw on projects, or unlimited time to figure something out, you kind of go with the easiest path. It’s like water. Water will flow from high to low on the simplest path down. When you don’t have money, time, and people you have to hit your head against the wall a lot harder. More often than not I think the best products, teams, and work – the stuff that actually changes markets – can only be created if you are truly forced to do it. I have definitely found that limiting yourself intentionally allows you to be a little more introspective and mind heavy versus resource focused, which I have seen results in higher quality outcomes…At the end of the day it forces you to focus and prioritize. If you are making smarter and better decisions on an hourly basis because you are forced to think harder and say no more often, the trajectory of what you are building will likely have a much better outcome.”
  • On a visualization framework to take risks: “When you are making decisions about your life, especially unconventional ones, you are constantly in a state of questioning and self-doubt. What I have often tried to do is imagine the alternative outcome: So, for example, if I didn’t leave school and pursue a path of entrepreneurship and I stuck with what everyone else is doing, what would that life look like? What would that option look like? Actually visualize, think about and feel that. Does it feel good? Are you comfortable with it? If you aren’t, it gives you so much more confidence and reassurance taking a risk because you know that the alternative is actually not an option that you are okay with. The mental conflict of evaluating decisions can be really overwhelming. Actually visualize the safe option. Really visualize it. Imagine yourself in it and whether you’re happy and if it’s getting the best out of you. If it’s not, that option of comfort and safety starts to crumble and gives you more confidence.”
  • On the trait that allows you to punch above your weight: “I actually think one’s ability to be in a situation comfortably while being wildly uncomfortable is super important. It comes down to one’s ability to know what to do in any circumstance and be comfortable figuring things out. It’s a little bit of this chameleon-esque concept of being able to sit in a room among people who may be way smarter than you, confidently sit up straight, even if you no clue what is happening, and hold your own. Sitting in the room, in and of itself, is a really important trait. Being able to have a conversation that is wildly uncomfortable with a straight face and even say: ‘This is wildly uncomfortable’ is an important trait. In a lot of our business and personal lives, that capacity to endure that pain and do it with calmness and a degree of composure is an overlooked quality. To me, that has by far been one of the few qualities that has helped me punch above my weight class, so to speak. It’s not saying you are confident, comfortable, or you know what to do, because you don’t. It’s acknowledging all of those things and then saying: ‘Given all of these factors, I can still maintain my calmness and comfort being in that situation.’”
  • On faking it forever: “Some people call it imposter syndrome. I just call it life. When I left school I was 19, leading product for a startup and pitching one of the most incredible venture capitalists in history. He was on our board and it was entirely terrifying. What we are pulling off today at hims is in a lot of ways also terrifying and the team is terrified. It’s just acknowledging what you are doing and appreciating it and then getting back to work and figuring out a way to get a little more comfortable with it. There’s the common saying: Fake it until you make it. What I have found is, if you are really making it, you are constantly putting yourself in increasingly uncomfortable positions that you have never been in. Your pace of learning is growing as is the magnitude of your experiences. I actually tell people: Fake it forever. That’s the reality. As you grow and what you are doing grows and becomes bigger and hopefully better, the opportunities, the people, the money that you’re going to be working with are also going to grow and you are going to be just as uncomfortable as you were that first time pitching for that first $100,000 seed check. That’s okay. It’s about being willing to continually have that state of mind and put yourself in those situations.”
  • On acknowledging fear to combat it: “It is a little bit Zen and meditative but I think it is an anxiety management concept which is a really important concept for life: You are constantly battling all types of things internally and externally.  If you don’t acknowledge that fear is there it just continues to grow in strength, weight and fear. By acknowledging it and looking it in the face, it usually decreases a little and goes back to it’s normal fear level. The acknowledgement and acceptance of it is super important. I have found that is a really great mind trick in destigmatizing or disarming something that is otherwise growing to be very powerful and scary in your brain.”