How to Overcome Your Fear of Failure (feat. Patrick McKenna)

Hi, I'm Susan Drumm, and welcome to the Enlightened Executive, where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. And I'm excited to have Patrick McKenna with me today, who's done an incredible amount of personal and leadership development, but is also a highly successful entrepreneur and investor with a focus on emerging tech hub cities. Over his career, he's co founded four tech companies, launched two investment funds and invested in over 40 startups, raising 200 million that resulted in over a billion in exit returns. Currently he serves as executive chairman at Facet wealth and partner at Comeback Capital. Patrick founded One America Works, a nonprofit addressing the geographic economic divide, but by bringing people together through work and investment. So welcome Patrick.

Glad to be with you.

I'm so excited to have you here because of all the work that I know, just even a little fraction that you've done. And honestly, I want to say you're a model for me of a enlightened executive, or at least an executive on their path to enlightenment. And so I would love to hear from you what helped you the most in your journey to become a more conscious leader.

Well, it's great to be with you and that's high praise. So I sincerely appreciate that. Just thinking about the question, I've had just a great opportunity to be in a lot of different types of leadership roles. I started my career after college in the Army. I was an army officer and that's a very specific type of leadership. Served overseas for two of the four years that I was active duty.

And then I came back and I.

Went to investment banking and worked on Wall street for a couple of years. And that's definitely a different type of environment than being in the military. And after investment banking, I was off to Silicon Valley where I co founded a tech startup. And this is definitely, of all the three is probably the most challenging of the leadership challenges where we took something from absolute scratch, a sketch on a whiteboard. And my first company, LiveOps, we grew it to over 20,000 people over five years. And the challenges that we faced along the way really pushed me, honestly, as a leader, as a person and as a team member all along the way, and then most recently as an investor, identifying young startup teams, particularly doing it outside of Silicon Valley. How do you identify talent? How do you see what they need? And then as a philanthropist, this is adding another element to it where now people are motivated not by return, not by capital, motivated by something completely different. You know, and the thing that over, you know, this, this career, all these very different experiences, the thing that I have really come to understand is that love is a bigger motivator than fear. And while fear is a big motivator and has been unfortunately too much of a motivator in much of my career, particularly earlier, the idea of love and the idea of seeing the world bigger than yourself has been yet even a bigger motivator. And that's really the answer to the question of the transformation or the insight that has led me to really accomplish many of these things.

Yes.

Now that's something you don't hear very often from a financial services background as impactful in tech background, as impactful as you've been. Can you share more about one what you mean by that, but how you came to discover that? Because I love it.

Well, I think the fear of failure is something that we can all resonate with. And certainly earlier in my career, the fear of failing at school or failing in getting a job or failing in performing really motivated me through much of my career to the next gold ring as I was kind of moving through and up. And then there was this really amazing moment that I had where some point in our lives we kind of get, we get proposed the question. And for me it was after selling my shares of a company that I co founded and kind of hitting kind.

Of all the, all of, kind of.

The material measurables that you'd be looking for financial success, credit for success and accomplishment. That was objectively what I had set out to do. And this was the sale of my first company, LiveOps. And I remember the moment so clearly. I was in San Francisco, my place in Telegraph Hill, beautiful place overlooking Golden Gate Bridge and all these things. And I had this very clear moment where it was like three days after everything had passed, I realized that nothing had changed. All of the accolades, all of that great feeling of this is amazing. This is what I set out to do, the sense of accomplishment, achieve the.

Financial goal and the trappings of success that everyone would. That I want. Wanted and everyone else seems to want. Yep.

And at that moment I felt like.

I had a choice. I realized that I could either triple down, double down 10x down and go and chase more of that kind of material success and really pursue the fear narrative, the fear of not being enough, the fear of failure, fear of not achieving everything that I could, or I can actually realize that whatever was going on in the inside, the inside measures, the inside scorecard, the inside thing was on a different track.

And that was the question how was.

It that I can actually find sustained sense of satisfaction or happiness? Because the path that had led me to that objective success actually hadn't led to the internal happiness. And that led me on the path that has actually opened me up and revealed to me what it means to actually replace fear with love.

Yeah. So then what happened after that? So you have this moment that you realize, wow, everything I've been wanting or pursuing actually doesn't give you the inner peace or happiness that you may be searching. Where do you go from there? Because I imagine some listeners may be in that or maybe thinking, oh, if only I get, if only I sell my company, if only I get that promotion to the C suite. But you have that and where did you take it from there?

I was very fortunate to have somebody.

In my life, a family friend who had studied a lot of meditation, had practiced Zen Buddhism. And I kind of posed the question to him. He said, he gave me this analogy. He said, patrick, he says, you are like you're flying a plane and you're flying the plane and your hands out on the wing and you got the other hand on the tail and you got one foot out the door and you're holding on as tight as possible. You're holding on to try to keep the plane from crashing. He says, what you need to figure out is how do you actually let go? How do you actually let go of the wings and trust the wings and the tail and actually just grab the steering wheel to grab the rudders and just grab it and now fly the plane, inflamed plane more stable. And his proposal was actually to, to investigate meditation. And this got me on my path to actually starting a meditation practice. I dove right in and went to a 10 day silent Vipassana retreat in Joshua Tree.

That was your first experience of meditation? A ten day vipassana.

I started reading a book called how to Practice, which was just literally the same day that I kind of had this first insight. I just, this book popped up and my recommendations, it's a Dalai Lama's book called how to Practice. And it was pretty much a like step one, step two, step three. I started reading the book and I started practicing on my own and. But I'd actually never practiced with any outside person. I'd never been to a class or hadn't sat in group and things were working. I was actually starting to see more clearly my own mind start to see the things that were triggering me for fear. And that was what I did. I went out to, I signed up for this retreat and flew down to Palm Springs and went out and sat, sat in some cushions for, you know, 10 hours a day for 10 days.

And at the end, the insight that.

I took away was actually that love is a bigger power, is a bigger motivator than fear, and that it was okay to let go of the fear because I was okay. And then if I expanded my view of who I was serving, what was motivating me, that was actually more powerful than actually just the fear of my own failure. And then through the meditation practice, like practicing that and then truly being transformed. Now this is really important because knowing something and actually feeling transformed by it, this is a big difference. And so for me was actually to actually apply it, say, well, what motivates me? Like what are the types of things that I don't work on? And then I got this interesting idea here. Well, I should be focused on things that are worth failing at because failure is going to happen. So then like, how do I overcome that fear? It's like, well, because fear is always going to be there. You're just managing me, right? But now expanding my motivation. Instead of being motivated by myself, let's expand it to actually be motivated by all those around me. Let's make sure that I'm actually focused on ideas and problems that actually are bigger than just serving the small, narrow view of myself. And you just do step by step. And that actually led me to not only take on bigger challenges like do three more startups, initiate funds, leave San Francisco years ago and start focusing right now everybody's left San. Not everybody. Many people have left San Francisco, but I left San Francisco years ago, kind of pursuing this very simple idea that I should be applying my energy and creativity to things that are actually bigger than myself.

That's extraordinary. And that's the shift that we're talking about also in adult stage development, where you go from trying to heal the ego, identity and self image where a lot of leaders start and creating security or all these things for me, and now getting your attention off yourself and onto something more meaningful, knowing that you're okay, you're whole, you're fine, you're gonna like you said like let go. And then you put your attention on something outside yourself and that's really where the magic happens.

So that takes practice. Actually, this is something for your community here, is that it doesn't just happen in one, like flash. That's actually a false thing. It's not like flash. And all of a sudden you're changed. It's small steps. Oh, My gosh, I'm enlightened. It's small taps and it builds confidence because the first time I was kind of exposed to this, honestly, I was like, letting go. Well, if I let go of my ambition, if I wasn't ambitious, I'd still be sitting in my small town. Like, I grew up in this beautiful small town called Placervill, California.

Lovely place.

But it took a lot of ambition to leave. It took a lot of motivation to leave. And so what we're kind of swapping out here isn't that you're not going to be motivated to change yourself or others is actually the motivation of why.

Right.

So for me, when I look back at my history before, the question was it wasn't I would actually do anything different. This is a big insight for me was I wouldn't have done anything different. I still would have studied really hard and taken all the AP classes. I still would have gone to college and left my small town. I still would have gone into the military and taken on every challenge that I could. I would have just changed my relationship with the things that I was doing. Instead of operating out of fear, I would have been operating out of love and possibility and potential, trusting that I wasn't going to fear failure, but that actually all of these things would. You don't do. I wouldn't do one less thing, Susan.

This is the thing.

I would actually do everything the same. My relationship with why I'm doing it, sitting in the library, instead of going, I'm going to fail this test, be like, oh, actually this is a great opportunity to learn something or to show how much I know, right? Or going and getting the job on Wall Street. It wasn't that, oh my gosh, I need to prove everybody that I'm smart enough to get this job. It's actually, I am smart enough to get this job. And this is a really great way to learn the skills that I'm going to need either in this career in finance or whatever I do next. And so this is really deep insight that I've tried to live with ever since is actually I'm still ambitious, by the way. I still have a very long arc of trying to make change in the world. I've just changed my motivation.

So you mentioned that this is an ongoing process. It's not a one shot, hey, I just determined this and therefore I'm going to live my life like this. What keeps you on track with that or what keeps the process going such that you can continually choose love over fear?

So as we progress in our careers, we get different roles, and actually knowing the role we're in in the different organization is really important. And so at this point, I'm actually spending a lot more time helping others, kind of coaching and mentoring others. And this is actually an important part of how to stay on track is actually to see what role you're playing in an organization. Because leadership isn't always being the CEO or being the director sometimes. And many times a leadership role is helping those who need the help for the organization to actually achieve the big goals that it's setting out to. And so for me, it's really looking, where am I uncomfortable? What's causing me anxiety? Because as much as this podcast is called the Enlightened Executive, I am far from enlightened. Hopefully I'm on the path towards that freedom where every day I feel free and liberated in every decision, in every moment. But honestly, tasting that and testing that and knowing what that feels like is actually a way to know when you're not in that state. So moving out of a more direct operating role into working with others is a really interesting place to be, because now you have to actually expand your empathy even further, right? Because nobody can do it the way I can do it. You know that, right? Like, I know exactly what to do next. If you were me, but nobody's me. And so the challenge that I am working on right now is how do I help and transmit many of these things that I have learned for others to actually achieve their greatest success, how to understand their motivations, how to understand where their strengths are. And to do that without judgment, to do that through love, do that without me fearing that they are going to fail, we are going to fail. But actually applying the same framework, right, is that I sincerely want their success. And I think, you know, this is like when you sincerely want somebody's success and it's in your heart, they feel it, they trust you. And if you. If you have some doubt on that, they will put resistance up. You will feel the resistance. So the daily practice of meditation for me is really staying concentrated and being present with those feelings. Anxiety, fear, that pops up. Also tension, ego, things like that, that can come up and keep you off that path of love and openness and just continue to trust it.

So when that happens, so you're meditating, you're getting present to what might come up in terms of anxiety or fear. What do you do then?

This is really where mindful practice comes in, is actually noticing it and just noticing where it goes. Because usually there's Something deeper underneath it. And this is really. This is the practice. Right. So once you notice it, you say, where is this coming from? Is there something else below it?

Right.

And then kind of reframing and stepping forward. So I don't know that I am the practice enough teacher on this particular. What I do is just observing it and noticing it and knowing where I want to go.

Right.

So I want to stay out of the kind of the narrow view of.

Myself and stay in.

Stay as much as I can in a broad view of all of us together. And usually those are the tension that I'm feeling when it kind of goes narrow. I'm worried about the outcome, the fear, this thing, and say, okay, usually that's an underlying thing. So if I notice it, I just say, where's that coming from?

It could also be the other person.

Right. The other person could be in a position where they're not receptive and open. And maybe it's frustrating and maybe it's not time. And so where I am right now with this, honestly, is balancing the difference between clarity and certainty. So having clarity of where you want to go, but being comfortable with the uncertainty of how you're going to get.

There.

This is the place where I think a lot of leaders, particularly as you advance in your career and you see the vision, you see where you want to go, and now you have to realize that you kind of step into the uncertainty of how are you going to get there? Yes, it's really. And the uncertainty is what drives a lot of that narrow thinking and that fear. And if you can stay clear but then yet comfortable with uncertainty, then you can actually find that magic. And frankly, entrepreneurism is the best training ground for this.

You don't really know how you're going.

To make it work.

But somehow, if you require clarity, I.

Mean, if you require certainty and outcome, you will not get very far. As an entrepreneur, you literally have to let go of the certainty, but you have to have a clear vision. And so kind of communicating and translating that, communicating that to others is actually a wonderful practice. But it's hard, not everybody ready to hear it. And frankly, many times it challenges myself because I have to actually be very comfortable with that uncertainty as well.

Yeah, I think what you're highlighting is such an important piece around changing your relationship with uncertainty. I've seen leaders try to double down on control when faced with those feelings of uncertainty, and that's worked for them in the past, but it's really inefficient. And as you said, it's Very narrow. And it will lead back to sort of the pain and suffering of a very narrow, ego focused approach to leadership. Whereas learning to embrace the uncertainty as even in a way a fun challenge, like that's how I try to turn it on its head. Like, can you actually make that fun? Like going on a, maybe a mystery trip with your significant other might be like, how can you actually make that aspect fun? But get really clear, what is it you want to experience, you want others to experience? Because the other piece that I hear come out very strongly, what you described is continually focusing on things outside yourself as well. So noticing what's going on internally, but also what's my clarity of vision for what impact I want to make in the world.

Advanced level, jokingly is actually to realize that you are part of that. You mentioned control, and I feel like this is one of the most important insights is that we have a lot less control than we think. What we control is our response. There's so much going on around us that we can't control, but we spend a lot of time on the things we can't control. And this is actually effective leadership. I don't know what the enlightened side, but to be an effective leader is actually narrow down the things that you actually have control over versus getting distracted by the millions of things that you have no control over. Those things you have no control, all they do is give you anxiety, grief and frustration. The things that you control, whether it's operationally, but also your response to them when a customer calls and, you know, doesn't sign the contract. Okay, well, you have a limited amount of, you control how you respond to that. You can't control, you can't get them to sign on the dotted line, but you can control it. When you have an employee quit and you really need them for a project, you can't get them back in there. You can control only your response to it. And those are two like, kind of like day to day examples, but so much of it. Do you not get the promotion? Did you not get the funding? There's so many things that you actually don't have as much control as you think you do over and you only control your response to it. And I think there's. I know it sounds simple, but there's a deep insight in operating as a leader in this position, in this framework of focusing on the things that you control. And the thing you control the most is your response.

Mm, yes. And taking that moment, I mean, even to the point of people trying to control traffic, you Think about getting frustrated and annoyed because you're stuck in traffic or somebody just cut you off. You can't control that. And yet we can get ourselves in such a tizzy about it. And you hear about some of the even more real road rage that occurs. All you can do, your efforts are better spent somewhere else because you can't actually control it.

That's a great way to practice.

What's that doing for you?

Right?

I mean, that's such a great way to practice this sense of like, okay, I'm getting frustrated because of the traffic. Okay, well, I have no control over it. Or maybe what do I have control over? I can get off of this exit.

Or I can maybe I can make.

A phone call, call your mom. It's something like you could do something else with the time. But getting frustrated with it is kind of a good metaphor for life things. Traffic happens and there's not a lot you can do about it.

Typically, yeah, it's how well you're going to surf that. So when you started down this path, what changed in your business then? Tell us a little bit about what your mission is now and why it's meaningful to you.

So a couple years ago I realized that I was living in San Francisco and had been like a lot of people at level of success as an entrepreneur, but I had spent a lot of time outside of Silicon Valley and working with entrepreneurs based in Baltimore and Atlanta, Portland, Maine. And I just realized there's so much talent out there and it suffers not only from lack of capital, but lack of access. And using this same kind of bigger perspective myself, I probably could have stayed in Silicon Valley longer, found more deals, done more investments and invested in that narrative actually looked a little bit broader and said, well, what is it that's worth failing for me? And for me it was actually to look at this broader insight to say there's talent everywhere, there's an opportunity gap in the country where not everybody can come to Silicon Valley, but these talented people all over. And what can I uniquely do to broaden this perspective and help people in different places get access to capital, get access to knowledge networks? And so I kind of set out to do that with some investing, some angel investing, seed investing, building networks. And it just became more and more sophisticated to the point where I moved to Austin, Texas a couple years ago to be closer to that market. In fact, my last company, the One Facet wealth, which I'm executive chairman, started that initially in Baltimore, Maryland. And again, this is like non obvious thinking, but applying these techniques lead to opportunity. I'm here to be successful in business. I'm not your guru. Like I am not here to actually write a book about self help. I am here to actually execute. I am here to make better investments, to start companies that I care about that I think are going to be financially massively successful, but make change in the world that I think is going to be worthy not only of my time, but of my potential failure. And so kind of following that same kind of path that we talked about at the beginning has led me to take on more opportunities and actually interesting see things before they've come. Like what happened in the last year during the pandemic, everybody moved to everybody else. Like remote work is everywhere. Capital is flowing to places like Pittsburgh and Nashville and Austin is actually a boomtown. And actually just following that same sentiment.

Of like, where's the bigger perspective?

How do I personally connect to it? Not saying like who is. I'm not trying to impress somebody by staying in Silicon Valley and doing a bunch of different things that other people would be impressed by. I think those are impressive, by the way, Susan, to be like an angel investor or early stage investor in those amazing companies. Amazing, terrific. And a lot of people should do it. For me, it was actually what motivates me. How do I apply my broader perspective to something that I uniquely have insight to that led me to this. Investing, starting companies and then ultimately starting a nonprofit called One America Works. And again, the idea there is, there's talent everywhere, it's under connected, it's under capitalized. And if I can take what I know from Silicon Valley and expose more people in more places, then we can kind of bring the country together. We call, you know, when America Works Together America Works. That was the insight. And it turns out to be a very good business model because there's talented people operating at lower costs with lower cost of living. And it's all kind of happening now. And so I think that that's kind of the takeaway for the audience here is that living in this love motivation, and I mean love by like something bigger than your self motivation is actually a good investment thesis because you actually see the world more broadly. We narrow our interests, we narrow our perspective and so broadening it out. And then here's the thing that's hard walking through that doorway and trusting it. Because I'll tell you, a couple of years ago it wasn't so obvious that the investment thesis of investing in Austin and Baltimore and Pittsburgh was going to be the thing to do. Now I don't know if it's going to be the thing to do 10 years from now, but it certainly feels like it's the right thing to do today.

Yeah, absolutely. And so it allows you to create that visionary aspect that more enlightenment and less narrow focus will allow. So what's next for you on your enlightened journey? What are you working on personally or professionally in terms of your development?

So the two things I kind of covered a moment ago is really practicing clarity without certainty. And I have set out this, what I think is a clear vision for myself of bringing people together through work, investments, more people in more places participating in the modern economy as a way not only to create great businesses, but also to bring us together as a community society. That's my clarity. How we get there. I started the nonprofit doing a lot of action, writing articles, building networks. I started an investment fund called Comeback Capital, which is a scout fund to do early stage venture capital in kind of the heartland areas. Also did an Opportunity zone fund to build affordable housing. Raised $150 million for affordable housing in emerging tech hub cities. Who knows what's going to happen with all these things? This is the uncertainty, but all of these actions are leading towards that clarity.

Well, where can people connect with you if they'd like to do so?

LinkedIn, which is a great place. Also one America Works has a newsletter. We have a couple things there. It's called the Midpoint. You can sign up for our newsletter. It's just twice a month we give great updates on emerging tech hub cities, what's going on from investing to company growth. Then we have a podcast there called the Bridge where we interview local leaders, entrepreneurs in places like Pittsburgh and Nashville and Indianapolis, Baltimore, and tell their stories. And so you can catch me at one America Works or at Twitter. Also, I think my Twitter handle will be somewhere in the notes because I don't remember it.

All right, perfect.

Yes, we can add that and really.

Appreciate you taking the time to share your journey and truly, I believe, a role model for future executives and entrepreneurs and tech investors, what you're doing and the shift that occurred. So thank you for taking the time to do that today and sharing that.

Thanks for having me.

And if you loved this episode, you'll also love my episode with Dena Kaplan, who is how I know Patrick, who shares her story about becoming a more enlightened leader through meditation and the new business she's built teaching others meditation. Thanks so much. Hope you enjoyed today's episode and I'd like to point you to the next important step hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive.