Lessons Learned From Taking Risks and Embracing Failure
About This Episode
In this episode of "Out of the Comfort Zone," I had the pleasure of joining Wanda Wallace to discuss critical aspects of personal and professional growth. We explored the concept of redefining risk, not as the potential for failure, but as the opportunity for success. I emphasized that the greatest risk is not giving oneself the chance to succeed.
Wanda and I talked about the importance of embracing failure as a valuable learning tool and the power of supportive relationships. I introduced the idea of the "critical few" – key individuals who significantly impact our lives. We also discussed the importance of focus and how concentrating on a few critical aspects can lead to more meaningful accomplishments.
Finally, I shared my "side door principle," which encourages finding unconventional paths to achieve goals, and stressed the significance of aligning actions with one’s values. This episode is packed with insights and practical advice for anyone looking to thrive outside their comfort zone.
Episode Outline
(01:26) My career highlights: Physician, scientist, engineer, entrepreneur, educator
(03:01) Helping others reach their potential and the importance of giving back
(04:41) The untapped potential of top graduates
(07:17) Redefining risk as an opportunity for success, not fear of failure
(10:24) The importance of supportive personal and professional relationships
(18:19) Failure as a valuable learning tool and inevitable part of the journey
(23:52) How to concentrate on a few critical aspects for meaningful accomplishments
(32:03) “The Side Door Principle” and finding unconventional paths to achieve goals
(40:49) Understanding your values and aligning actions with them
(55:08) My advice for embracing authenticity, building strong relationships and taking aligned risks
Resources
Connect with Mike
Follow Mike on LinkedIn
Subscribe to the Northpond Newsletter
Connect with Wanda
About This Podcast
Out of the Comfort Zone features carefully-selected guests and expert practitioners who discuss their own leadership journey and offer practical tips and insights to help you develop the confidence, new skills and methodologies you'll need to survive and thrive when you step out of your comfort zone.
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Wanda Wallace 00:06
There is no growth and comfort and no comfort and growth. Yet the big leaps are how careers are made and how businesses Excel. So how do you master not knowing at all or feeling like an imposter? How do you have the conversations that will lead to trust? And of course excellence? How do you take charge of the things that you can control? How do you thrive outside your comfort zone? That's what this podcast is about. I'm your host, Wanda Wallace. And it's time to get out of the comfort zone.
Wanda Wallace 00:36
Welcome to out of the comfort zone, or a growth mindset, getting out of your comfort zone taking risk, perseverance, willpower, these are all adages that you hear every day that describe how to succeed. And I'm sure you've heard those and many, many more. But today, I want to ask the question, what if we're thinking about these in the wrong way? And how do you think about risk? And how do you know if you should persevere at something or change course, by the way? And how do you keep from burning out all highly relevant questions for everybody that I'm talking to, at least out there in the work world, whether it's an entrepreneurial world or a corporate world. So we're going to take a page from a leader who's learned a great deal about success from establishing over 100 companies, and I did say that correctly establishing over 100 companies.
Wanda Wallace 01:26
So my guest, Mike Rubin, wears many hats, physician, scientist, engineer, entrepreneur, and educator, and above all, a devoted husband and father. He's the visionary founder and CEO of North pond ventures, which is a science driven venture capital firm, where Mike spearheads multibillion dollar enterprise dedicated to fostering businesses with the potential to revolutionize science and human health. He's done quite a few things in his career, as you're gonna hear shortly, including founding another venture capital fund called sands capital ventures. And prior to doing all of this work, he was a board certified physician and surgeon completing his fellowship training at Harvard Medical School. His educational background includes an MBA, the obviously the medical doctorate, and an electrical engineering degree from UCLA just to name a few. Mike, welcome to the show.
Mike Rubin 02:25
Thank you, Wanda thrilled to be here with you today and look forward to our conversation.
Wanda Wallace 02:30
I'm also looking forward to this, it's a little different than what I usually get from my guests. In fact, most people have a book or some coaching services or something that they are hoping to sell, not that we actively sell it. But you know, visibility helps increase this. But you're not here to sell a book or services. In fact, no one's actually going to call you and say, Hey, Mike, would you help me with my venture capital? So why do you want to speak to my listeners? What do you want people to understand?
Mike Rubin 03:01
The number one reason I want to speak to your listeners is to help share some of the things that I learned along the way to support them reaching their potential. I'm incredibly fortunate and grateful to have achieved a few things that I've aspired towards, over time, and I am an educator, in part. So I am on faculty at at Harvard, MIT and Stanford. I'm a visiting scholar at at Harvard and MIT. I'm an adjunct professor at Stanford, I work with a lot of students, I teach courses there on intrapreneurship, and specifically in entrepreneurship related to to science. And that has been incredibly well received. And as a result, we founded an internship program and a fellowship program where we bring in a lot of the students, whether they're undergraduate students, or doctoral students at at, at these three institutions, and they benefited from it. But I realized not everyone goes to Harvard or MIT or Stanford, not everyone's a PhD student there. Not everyone can do our internship and fellowship. And I just get a very large number of solicitations about all sorts of questions that have less to do with technical matters, accounting and finance or scientific matter, but more about how do I go about doing it. And I felt like a forum like this, what allow me to share to share some of these insights beyond what I can in the physical classrooms that I participate in.
Wanda Wallace 04:41
I love that. And I appreciate that message of sharing and as part of my life mission here and the reason we do this podcast. All right, one of the things you said we're talking about is potential and helping people achieve their full potential and you talked to me earlier about under stating that MIT graduates, for example, were amazing high school students, but then they graduate and they don't do anything all that dramatically interesting. Explain your point of view and why you think this potential is so untapped?
Mike Rubin 05:16
Yeah, I'm incredibly privileged to work with these extraordinary students at the leading academic institutions in the United States if if not in the world, and the threshold to gain admittance to these places, is just extraordinarily high, right? Like, you know, places like MIT or Harvard, they have students who either missed no points on their standardized tests, or one point, right. And then on top of it, they do all these extraordinary things that are truly exceptional and intrapreneurial. And whether it's music or athletics and different academics, and so they, they come in being extraordinarily innovative, and creative, and individualistic. And they get, they get selected that way. Wow, that's pretty cool. Yet, on the back end, what I observe is, the vast majority of them ended up taking professional opportunities on the back end of graduation that are a bit more predictable.
Mike Rubin 06:20
And I won't mention the specific firms that tend to hire a lot of these grads because I work closely with them. And I admire them, and they're great firms. But I feel like there is an opportunity for a lot of these extraordinarily capable people to bet on themselves a little bit more to take what would conventionally believe to be more risk, so to speak, to better leverage their talents. And so when I talk about return on potential, when you have this much potential, the return on potential can can be really substantial. And I want to be an agent to help support people on that path towards maximizing what what they're capable of, as opposed to playing it safe, or doing what's expected of them. Or, Hey, I gotta get 100% all the time. And if I go outside this box, that that might not happen.
Wanda Wallace 07:17
So is this about getting more people to start more businesses? Or is this about just taking a risk and trying something new, even in a traditional job? I mean, how would you qualify that somebody's really achieved their potential? Yeah,
Mike Rubin 07:32
that's, that's an excellent question, Wanda? And the short answer is no, it's not just about entrepreneurship, that's obviously a big part of what I do. And I'm a proponent of it. But I just look at entrepreneurship as a vehicle, if you will, to express whatever it is that you have within you in, in a unique and authentic way. But it's not it's not the the only vehicle. And I think what people need, in particular, early on in their career, especially people who have very rarely failed at anything is permission to fail, and not just permission to fail. But actually convincing people that failure is an inevitability. And then once you accept the inevitability of failure, sometimes you'll fail privately, sometimes you'll fail publicly. And sometimes you'll fail publicly speak in a spectacular fashion.
Mike Rubin 08:34
And that's okay, too. People actually love you more for it, is the reality of it. As you know, when you're honest about the things that you've done, that didn't quite work, you know, the capacity for human compassion, compassion is extraordinary. But once people feel like they have the understanding that they will fail, then it's not a function of, hey, what if I fail? What if I don't fail? It's, well, if I am going to fail at times, what do I want to fail? At what what is worth actually having that experience on? And, you know, the answer is, it's worth baling in a way where you are pursuing things that you're passionate about, which are authentic to you, and which allow you to reach your potential. And that's what I try to emphasize with people that I work work with.
Wanda Wallace 09:24
Yeah. All right. So I played have played this game for decades, decades with very senior leaders in some of the world's largest corporations and asking them to say publicly, what was a major setback in their career? I have yet to find a single person who doesn't first laugh and say second, which of many, and some of those have been public everywhere. And some of them have not been so public and some of them been an honest mistake. I mean, it just happens and some of it has been some mistake that they made or somebody else made. made. So I think I think you're right, that failure is part of the package. Now, why do you think we're so afraid of failures because we haven't failed or we have the wrong mindset.
Mike Rubin 10:13
I think the fear of failure is a function of what we learn repeatedly. As as we grow up, and as we develop, and what we get rewarded for, and how the system works. Right. So we talked a bit about academia, which is something that I, I spend a lot of time on. But the system is designed and select specifically for people who almost never fail. Right? That is the system right? Is sometimes it's pretty, pretty quantitative, right? And it doesn't reward a lot of risk taking of, Wow, I tried a lot of things, and they're really hard, and I wasn't good at them at first, and I got a really, you know, I didn't perform well. And here's all the times I didn't perform well, but don't worry about it, I learned a lot from it. But yeah, I, you know, I didn't have 100% on everything that I did, like, the system basically looks at those people as people who are of lower potential, right.
Mike Rubin 11:17
And so what the system rewards is people who have maximized the level of sort of success at a very young age. And statistically, in order to do that, you one have to conform to what's being asked of you, you have to conform to the system, okay, you got to study this information, you got to take this class in this order. And you got to learn this syllabus material, and you got to get, you know, 95% or higher on this particular test, and you got to take these standardized tests. And that's how you get in and it gets reported, and all this stuff is required. And that's all well and good. But then asking those individuals to behave differently, you know, once the reward system has been inculcated in them, to achieve these things, is extraordinarily difficult, because that's all they know. And you're actually self selecting for people who have that mindset. And so it's not surprising that it's really hard to disavow them have that that sort of philosophy.
Wanda Wallace 12:28
Yes, and I see those same people coming into my corporate clients. And the first several years are kind of a little bit of a ladder. So they do everything that's expected in that first year and a little bit more and in the second year and a third year in the fourth year, and they get rewarded accordingly, until you hit that moment, where now we want you to step out of the box a little bit. And suddenly, then they kind of go, Ah, I can't I don't know how I'm afraid I can't fail. And it just, it perpetuates itself, all the way into the world. It's a world of work, right now you have this belief that we have a wrong view about taking risk. So tell me, what's wrong with our approach? Well,
Mike Rubin 13:15
I would start with what, how most people define risk. Okay, most people define risk as what if I try something and I fail. So that's what they think about and they say, Wow, that's risky, because it may not work out, and therefore I won't do it, even though the reward is really compelling to me. And what I encourage people to do is change their definition of risk. And again, number one, risk to me isn't trying something and failing, the biggest risk I could take in life is what if I have a shot at doing something that's meaningful to me, and I don't give myself that opportunity. That's risky. It's really risky. Living your life, not providing yourself the opportunity to do the things that you are passionate about, because you're concerned about what the outcomes might be.
Mike Rubin 14:14
And, again, one way to sort of alleviate the concern about the traditional concept of risk of what if I fail is to is just to embrace the inevitability of failure. It's not to tell people Oh, don't worry about it, it'll be fine. You'll you know, it all work out like people won't necessarily embrace that sense of certainty, that everything will work out perfectly, and they'll, they'll achieve everything they they strive to achieve. What you just have to convince yourself as you're gonna you're going to experience ups and downs and wins and losses, either way, so you might as well do the things that you want to do.
Wanda Wallace 14:57
I love that we're going to have wins and loss is we're gonna have failures, we're gonna have setbacks, we're going to have brilliant successes, regardless what we do, why not put it to bear on the things that you want to do? Now? How do you say to the people in your life, whether that's key partners, or family members, or mentors, or stakeholders, for that matter, I'm gonna go do this thing that I'm passionate about. And because I have to give myself an opportunity, and I'll take the failure along the way, and how do you, how do you convince others to back? Well,
Mike Rubin 15:31
I think it starts by trying to surround yourself by like minded individuals who believe in you and support you and being selective about creating an ecosystem around that. So I'll give you an example for for myself, I spent 10 years in medical training at the doctoral and postdoctoral level, I became a board certified and licensed physician and surgeon went all the way through my training, and ultimately opted not to pursue a career in clinical medicine and took a pretty sharp pivot into the world of investing in finance and entrepreneurship. And at the time, when I had made that decision, I was newly married, and I had a son who was less than one years old. My wife is also a physician, a graduate of Harvard Medical School, and as like, five diplomas from Harvard Medical School, and she was a fellow there at the time as well.
Mike Rubin 16:35
And I was unhappy, doing what I was doing, I was unhappy, and I didn't feel like I was in my genius zone. You know, and I, I conveyed that to her, and she just completely didn't bat an eyelash, like, she just married me, we had this kid, I spent 10 years she thought she was marrying this position, she's like, Oh, well, then just don't do it. Like do something else. Like, you're gonna be amazing. Like, you know, I support you completely, I encourage you, I actually encourage you to, to pursue the things that you think you're best at, and you're passionate about. And, you know, I support you, and I believe in you. And, you know, it's, it's hard to overstate what a huge difference it made to, you know, be around people, let alone, you know, my, my wife, who believed in me and supported me and encouraged me to do the things that I was best at and passionate about. So be really mindful of who you surround yourself with. They can influence how you how you think and what you do.
Wanda Wallace 17:41
Yeah, absolutely. And maybe some you spend a little less time with until you've had some small successes, and then you can come back around, many people will get back on the bandwagon when they see that you're really happy and succeeding. All right, you said some words in there, you said, passionate and good at ingenious seven. All right, and here's my question. I can be passionate about something. But I'm not skilled at it. So how do I know if I should just stick with it and pursue it? Or whether that's just never going to be the thing for me? Yeah,
Mike Rubin 18:19
that's, that's such a fantastic, you know, question, Wanda. And sometimes, you have to pursue things in order to learn, and then have the acuity to understand where you are, and make the right decision. And oftentimes, the best way to learn things in life is just to do them, right. There's just no learning that's better than then experience. And there are certain times in your life where you have to decide which is the right paradigm. Sometimes the right paradigm is perseverance. And what I've learned more often than not, is plan a generally doesn't work. So don't get too attached to it, right. Like, generally, Plan B doesn't work. If you get Plan C to work, you're lucky, right? And so I don't often fuss too much about Plan A when I go out at something, I don't necessarily expect it to work. I take the plan that I think is probably most likely to work. But I know I need to iterate.
Mike Rubin 19:28
And sometimes I don't need to just iterate I need to take an entirely orthogonal approach, because what I'm doing isn't working. And it's really having the acuity to try things but then to be intellectually honest with yourself and ask yourself, Is this working? Is it not working? If it's not working? Why is it not working? And sometimes to your point, there's an old saying, it doesn't matter how fast you climb the ladder if the ladder is leaning against the wrong wall, you're only getting farther from where you want Be and you need to have the acuity to determine and ascertain whether, you know, so to speak with the skills that the ladder is, is leaning against, against the right wall, what what I find is, most people who are deeply passionate about things more often than not find a way. You know, it's generally not super power intelligence, right, or superpower strength, there are things that require that, but 99% of the things that people are passionate about, are achievable for them, but it's not going to be Plan A or plan B or Plan C. And you know, to your point, you have to have that flexibility, right, just
Wanda Wallace 20:43
to having this conversation with my god children about as they're beginning their college careers, and not being afraid to really be passionate and to really go for it. But then if you're gonna go for it, give it like, do all the steps that you've got to do and don't be afraid of those steps, because you're not yet good at it. But then that acuity, presumably, knowing if I should continue, or if I should pivot comes from having the right people around me. Is I mean, is that it just having talking to lots of people lots of occasions and saying is this working Where's plan Q.
Mike Rubin 21:21
The best teams, when Wanda and having the best people around you is absolutely the best advice that I could give to anybody, you don't need to know everything. You don't even need to be an expert at most things, you need to surround yourself by people who are complimentary to you, who you work well with, who can both mentor you, as well as work collaboratively with you to achieve a shared vision. And maybe there's elements to what you're trying to achieve that you're not the most skilled at, I certainly am not the most skilled at the vast majority of things that our organization has to do in order to win, right? That's literally impossible. You know, because there's just so many different facets to what we do. But that's why we have a team of highly capable people who work collaboratively towards a shared vision and, and mission. And so working with great people is, is really, really critical. Yeah, I
Wanda Wallace 22:26
music to my ears, that you out of the comfort zone moves for me are about knowing some things, but not knowing everything. So let's dig into that one for just a minute. Because one of the things that you've said, is you have to know some things. But it's surprising how little you have to know explain your philosophy here? Well,
Mike Rubin 22:47
I'll give you an example in my industry. So we build businesses around scientific constructs, which is really exciting. And really interesting to me, and I have some aptitude in that capacity, I have two doctoral degrees in MD and a PhD, I have an engineering degree, I think and do science all the time. But at the same time, a lot of this work is so esoteric and so specialized, that there's really no way that I specifically can be an expert on every single construct that we look at. Oftentimes, there's only a select number of people who can be an expert at these things. And so what I need to do is I need to learn how to interface with people who have this expertise, and ascertain whether we can leverage this expertise in a translational manner, in my case to develop commercial enterprises out of it. That's, that's what we do. And so I don't need to know everything, to use certain things, but I do you need to have the appropriate intermediaries. And I do need to be able to speak with people in a way where I can get what I need. And so that's really, in my profession, at least what's what's most important is to be able to understand what the right questions are to glean the relevant information and to make the right decisions based on getting information from people who are experts.
Wanda Wallace 24:17
Okay. All right, the right questions. I think you can get all sorts of things done if you have the right questions. But that is not just a matter of saying, Well, what's going to work here. So how do you go into a completely new technology? You know nothing about it? How do you go about preparing to make sure you're asking the right questions?
Mike Rubin 24:36
Yeah, in my industry, we're very systematic about it. So we realize through the work that we do, that there are certain criteria that have proven to be relevant. So for instance, we look for constructs technologies, platforms that are sustainably advantaged and differentiate If they have to be better, and they need to be sustainably better, otherwise, they're going to be disintermediated. By, by other constructs out there. So we look at a lot of interesting science, the question we have is, why is this a better solution than what's already out there. But that in and of itself is just one criteria, and it's necessary, but it's not sufficient, we then need to look at the underlying market and the underlying customer and ask ourselves, is this a solution that a meaningful set of customers need? Okay? Or is this just a really whiz bang, very cool technology solution to either a problem that no one has, or the business model doesn't work?
Mike Rubin 25:48
So the technology is so expensive, or there's some facet of the business model of how we would actually commercialize it, that from a financial economic standpoint might make it prohibitive to actually build a business around it. So these are the kinds of questions then we look for management teams and individuals who are focused. Focus is a huge word for us. Because when you're an entrepreneur, and you're a scientist, you're excited about so many different things. And you think about all these infinite possibilities. But at the end of the day, when you're trying to build a business around it, it requires a tremendous amount of discipline and focus. And that is rare, so rare that people ask us, Well, how do you define a great management team? And to me for the work that I do, it's people who are one focus and to have the ability to execute, so they know what their job is. And then every single interval time, when you meet with them, they're executing against their job, or if they're not, they know what the delta is. And they, they have rational plans to sort of fill that gap. And those are the kinds of behaviors that we look for in entrepreneurs, right?
Wanda Wallace 26:57
It's interesting, every entrepreneurial company, I've interfaced with bar one, every one, whether it's I've talked to the founder or just talked to somebody working there are lacking focus. So anybody out there, I think that's true and large corporation, you're trying to get something done, you have got to be focused, otherwise, you waste more time than you can imagine. And you take precious resources that then don't go to the execution. And boy, do I see that every day of my professional life? Alright, so right questions. One is, how big is the problem? Is it commercializable? Meaning can people solve it? Is it unique, sustainable, and will be unique for a while so that there is time to actually build this and make it work and grow it? And then do I have a team in place? Who can be focused and are actually disciplined about getting through the execution steps that they need to get through?
Mike Rubin 27:56
Absolutely. All right. Now,
Wanda Wallace 27:59
it's a new technology, let's say it's in a whole area that you've never really studied something very specialized? How much do you worry about understanding the technology per se? You personally, how much do you worry about that?
Mike Rubin 28:14
I worry about it to the extent that one, I can trust the people on my team to do the technical diligence, and I can ask them the right questions. And I know what the right questions are to ask. And then I can make an appropriate assessment at some level, whether we're cognizant of or not, even for things that aren't technologically sophisticated. We rely critically on people around us, right? Like when you're driving a car, right? You know, you're critically relying on all the people around you to do the things they're supposed to do so that you can get from point A to point B safely, right? Like you, it's hard to imagine how many basic things that you do in your life, when you don't even think twice about that you are critically relying on the expertise of others. Every time you eat a sandwich, there's just so much expertise that went into that, and so many assumptions that you're making about, you know, that that that that sandwich being, you know, properly, you know, prepared.
Mike Rubin 29:19
So, so that, you know, it, it's not tainted, you know, or a whole host of things that you might imagine. And so, in our case, it's no different. It just seems more esoteric, and it seems more technical. But like I said, you have to have trust in the people, right? Implicitly you you kind of, you know, trust the FDA with medicines that they've tested and they tested it appropriately. And people put their lives on the line for all sorts of clinical trials. They don't read and they don't understand and people who have expertise that like, you know, and they're not making like small decisions, right? They're making life altering decisions based on you know, trusting people who are credible And so, you know, we, to some degree always have to do that we do that within our organization. But again, if I can't ask intelligent questions and get confident about the answers and feel like I'm making an informed decision, then I'll defer because then we're not the right organization to do that, you know, and we're not trying to do everything we're trying to do what? What's in our wheelhouse, right.
Wanda Wallace 30:27
All right. So I get the asking the right questions, I see a know how important that is. I see it all the time. I also know that there is some experience that tells you what the right questions are. So it's taken time, I'm presuming for you and your business to say, we have to know the size of the market, the sustainability of the technology, etc, etc, that you just articulated that any advice for getting a better set of questions so that you are getting the right information to make the decision you have to make as a leader?
Mike Rubin 31:00
Yeah, that's, that's a great question. And I'll answer it in in the following way, especially given how much the world has changed over the course of the last few years. One of the best ways to get the best questions, and then the reason ask the best questions is to get the best answers. Right. So that's, that's the goal of the question is to get them answered and get them answered in a way which gives you the information you need. And the question is, how do you do that. And I would take one step back, and I am a huge proponent of showing up. And it sounds like an obvious thing. Yet, a lot of people in life and in business, don't show up. They don't show up to their kids soccer game, there's a business meaning they don't show up. And then when they do show up, they sort of show up, they're kind of there. Right? So how do you really show up? Well, you got to do two additional things, you got to be prepared.
Mike Rubin 32:05
So you don't just show up to something. But you show up prepared, which means you've done your research, you understand what the opportunities are, you understand what the challenges are? And you ask informed questions, right. And so if I work with an entrepreneur who has a really desirable business, and one person does a phone call, says, Tell me about your business, and then ask some questions, which are sort of obvious. And the other person says, Wow, this is amazing. Would you mind if I fly out, you know, cross country and meet you in person, I'm really excited. And then that person shows up, and then asks really intelligent questions about the business, that's just going to make an entirely different impression.
Mike Rubin 32:51
And then the third thing is, not only do you need to show up, and you'll know you need to be prepared, but you need to be passionate, because in my industry, intrapreneurs are oftentimes giving up a lot of, you know, comforts of a more predictable path to do something that they're passionate about. And they're looking for people who share their passion and who truly want to be on this journey with them. And you need to match their passion in order to be a desirable partner. And so bringing it back to the right questions, you got to have the right forum. And in order to have the right forum to get the right answers, you got to show up, you got to be prepared. And then you got to be passionate. And then once you do those three things, the right questions kind of become easier. things, you know, flow more smoothly. And you you get more intellectual honesty on both sides. Yeah.
Wanda Wallace 33:53
Yeah, there is that human engagement, genuine curiosity, we often say, passion, with preparation that says, I'm here, I'm paying attention. I mean, to be here, I want to understand what's happening. And one of my favorite CEOs often says that, you know, sometimes you just have to ask the dumb question, because sometimes the dumb question is the one that is really ultimately the smart question, and in his case, it was largely I don't understand how this reconciles with something you said before, it doesn't make sense to me explain it to me and turns out, you know, people can't always explain it because it doesn't always make sense. So it's, I love that so that it's showing up fully showing up prepared passionate in the right forum.
Mike Rubin 34:45
And I would also add if I may, you know, we have another another framework here at at North pond ventures are our firm, which we call the Sinequan on Yeah. Paradigm. I'm, I'm a fan of Latin so I I tend to Latinized certain things, but it means that which without it's what is the essential thing? And the reality is not all questions matter equally. And you don't need to answer a long list of questions, generally speaking, you need to answer three to five questions. But you need to answer them well, and you're better off only asking three questions that really, really matter. And getting really confident that you have a really good answer those three questions, then try to cram in 20 questions. And that's what I see all the time. With so many meetings and diligence, as you see these people.
Mike Rubin 35:39
They're generally earlier in their career, and they come in with the they're prepared, right? And and they come up with a list of 50 questions, and they're just trying to get through the list and answer these 50 things because they know that they're gonna go to some boss, and the boss might ask them anything. And they want to make sure they have all the information, where in my experience, you're much better off saying, here's the three things that really matter, right paradise principle 8020 rule, not everything matters equally. And I just really need to nail these three things and understand them really, really well and go into depth on them. Because chances are, if this works, or it doesn't work, it's going to be predicated on these three things. So I'm much better off spending all of my time on those three things than just trying to check boxes and go through a long list of every conceivable question. Yeah,
Wanda Wallace 36:27
I think that's one of the anecdotes of managing all the stuff that comes across anybody's desk, and being able to be productive and generate something useful at the end of a day or a month or a year. And that is focusing on what really matters. And it's just a passionate thing. For me, it's like not getting distracted by all the little things, even though I said the opposite when we were chatting before we started recording this podcast. But I like that, what are the three to five things that if we don't get right, we don't do? Well, we don't really understand. We're not going to succeed, period. And then the 20 or 30, we will figure out along the way. Exactly. Okay. All right. So show up really genuinely with curiosity with interest prepared, passionate about what you're talking about in the right forum, where people can converse and go back and forth. And then the cynic one non that which without focus on the three to five, that is really going to make a difference at the end of the day. Okay. All right, I want to come back, then I want to have a side doors. Okay, I'm gonna come back to perseverance in a minute. But don't talk about side doors first, because it's part of that perseverance thing. You know, part of the perseverance is I'm not giving up because I'm passionate about it, I believe in and I'm going to stay with it, I'm going to go to plan D, F, you know, XYZ, whatever it is, I'm going to keep going until I get it right. And you say lots of times people don't succeed, because they don't think about the side door. So explain your philosophy here.
Mike Rubin 38:02
Yes, this is, this is one of my favorite personal philosophies that I've I've learned through real life, and the front door is sometimes necessary to get into the so called Building if you if you will, but there's often a long line through the front door. And sometimes, you know, that's the only way through. But it's not often the case that it's the only way through, right, you know, sometimes you got to go through the the side door, you've got to, you know, jump through a window, right, go through the chimney. You know, life oftentimes affords you all sorts of different paths to achieve what you want to achieve. But it may not be the conventional path. And I think it's really important for people to sort of contemplate that because I can't tell you how many times I've been told that I can't do certain things that I've done. And the reason is actually understandable, because people look at all these conventional ways of doing things and say, well, this doesn't comport with the conventional way of doing things.
Mike Rubin 39:21
You're not fast enough to run the Boston Marathon. You don't have enough time to get your, you know, your PhD, you don't have a long enough track record to raise your your own fund, you know, the list, the list goes on and on about all the things that people are trying to convince me that I couldn't do for one reason or another. And the reality was, well, in some senses, if you're relying upon a really, you know, canonical, conventional approach to things then yeah, maybe the odds were a little steeper, but then I asked myself, well, what's a better way to be able to, you know, teach at Harvard and MIT and Stanford and still, you know, run my business and have time for my kids and run marathons and do all these other things. And if you try to do things conventionally, yeah, you're gonna run into some challenges along the way. But if you're willing to be creative and innovative, and try different approaches, you'll find there's more efficient ways to get what you need. And that's sort of what I call the the side door principle.
Wanda Wallace 40:29
Okay, so give me an example of a side door in your life, or in one of the companies that you've been part of. Yeah,
Mike Rubin 40:35
you know, I, I sort of rattled off a few. But I'll, I'll go into greater example to sort of explain what they are, right. And so I'm, I'm proud to run the Boston Marathon on behalf of, you know, an organization that I've been a part of, I raise money for children who have in inborn genetic defects that lead to blindness. And, you know, I trained as a as a retina ologists, so to speak at NASA pioneer and Harvard Medical School, and a lot of the Harvard institutions get spots in the Boston Marathon, and you can raise money for it, and you can run the race. If you don't have a spot like that, you got to qualify, in order to qualify, you got to be much faster than I am. And, but that doesn't mean you can't run the Boston Marathon, it just means that you've got to go through this other route. Right. So now I can run the Boston Marathon. I, you know, ended up getting my PhD on a part time basis, after already, you know, getting my MD and doing my doctoral and postdoctoral training, I was working full time at a wife and kids. So going back and conventionally getting my MBA or my PhD, for that matter on a full time basis while doing all these things wasn't feasible. But I found mechanisms to do it on a on a part time basis.
Mike Rubin 42:02
You know, I love I love teaching as an example. And you know, my father is a professor. So there was a part of me that aspired to be involved in research and teaching at these extraordinary universities. But at the same time, I'm a co founder and CEO of a multi billion dollar science driven venture fund. So I can also be a full time professor. But I found a way to develop a lab at Harvard University, we have our own laboratory, and we do research and I teach there, and I could still do what I do. But there was no conventional pathway, there was no sort of item that I could order off the menu at Harvard and say, Hey, I'd like this specific role that all these other people did you we sort of had to create it, we had to work within the system to figure out how do we each achieve our own respective goals and create a pathway here that that works. And these are all examples in my life of side door principals, and they get me what I want. They're gratifying allows me to have an impact, and allows me to engage in many more things. And otherwise, what if I was really constrained by doing things conventionally?
Wanda Wallace 43:05
Okay? All right. I love that idea. I'm a believer, if my mother has said of me, since I was a little that don't tell one to know, she will find a different way, which is a little bit. It has its own complications, but that is certainly my philosophy. At the same time, I see people who have very fanciful ideas of how they're going to make a side door work. And it gets a little unrealistic. So you know, one is let's cut a whole new hole in the roof. And I'll descend through a helicopter and you know, okay, possible, but unlikely. How do you distinguish between a plausible side door and a pipe dream?
Mike Rubin 43:47
Yeah, that's, that's a fantastic question. The best way that I've learned to distinguish between the two is to give it a go and see what I learned and see what works. You know, there are times where I felt like I had a great Plan A was really well thought out. It seemed not just plausible, but probable. And I gave it a whirl. And wow, you know, why did that not work? Right? It didn't go any, anywhere close to what I expected. And I had to, you know, turn around and figure out wow, I got it. I got to take a real different approach to this. And there's other times where I thought, This doesn't seem probable. Most people wouldn't even say it's plausible. But I thought it was possible, right? Those are the different concentric circles, right? Possible means?
Mike Rubin 44:44
Well, it's not ruled out by physics, right laws bowl means it could work. Probable means it will probably work. And then within that you have your sort of projected outcome. Here's what I actually think will happen. And, and I think to be intellectually honest and know where you sit within those concentric circles, and then make a calculated decision. Yeah, there are times where I know I'm doing things that are possible but not plausible. There are times that I do things that are plausible, but not probable. And there's other times where I say, Look, I'm going to, I'm going to, in this particular instance, focus on something that's highly probable to work. And it's just having the acuity Juanda, to get feedback, see what you learn, and then either iterate or persist or pivot. That's what it takes.
Wanda Wallace 45:42
Yeah, all right. So there's multiple steps in this one that I want to highlight, we're back to where you started with on risk. And this notion is not the risk of failure, but the risk of not really giving yourself a shot. And I think what you're highlighting in all of this is each risk is a learning opportunity. And you want to structure those risks to learn, so that you've got more, you see the plausibility and the possibilities and the potentials or probabilities coming through. So there's, there's all that there's this sense of surrounding yourself with people who are going to give you information you don't have and are going to give you the feedback you need, but not are going to hold you back. So there's an interesting choice there of who are the right people. And then there's the how do we have the right conversations? How are we asking the right conversations, and then you come to this just flat out willingness to keep reiterating. Just keep at it.
Mike Rubin 46:39
You know, it's amazing how much you can achieve. By staying in the game, right, you can't win a game you're not playing. So as long as you keep things in front of you, as long as you stay in the game, then you have an opportunity to effectuate, ultimately, a positive outcome. But as soon as you take yourself out of the game, then then you lose that opportunity. And more often than not in life, it's very hard to know what's right around the corner, right? You don't even necessarily know what tomorrow will will hold. And so you have to have humility around that. And you have to realize, well, maybe tomorrow will bring some unique challenges. But it might also bring some unique opportunities as well. And if I'm still in this game, it gives me an opportunity to then leverage what may happen to the future. To my my advantage. And all of that really is you step back and you make these decisions to me is is predicated on having clarity on a number of things, at least for me.
Mike Rubin 47:56
Number one, it's really critical to have clarity on what your values are. That is really the foundation and then secondary to values for me is being clear on what roles you want to serve in life, whatever they may be, those roles may be, in my case, being a husband or being a father or being an entrepreneur or being an educator or being a runner, a whole host of other things. What are the roles that you want to assume in life? Forget the outcomes for a moment, what journeys Do you want to be on, right? And then tertiary to knowing what your values are, and knowing what your roles are, are then setting appropriate goals that comport with those values. And those roles. And I want to modulate that by saying one really critical facet about it, because people talk about values, and people talk about roles and goals. But one thing that I found in life is really critical, is also to rank order them and prioritize them. It's not just enough to know, hey, I have these 10 goals. You need to know at the end of the day, what role is most important your life? What second? What's third, what's fourth? You know, great. It honestly doesn't matter how many goals you have.
Mike Rubin 49:24
People always ask me, how do you take all these things on at the same time? How many goals should I have? Is it too much to do all this? And I said, it's far less critical to count whether you should have three goals or 10 goals or 1000 goals. What really matters is Do you know what the order is? Because if you know what your number one, two and three goals are, well, then you're going to make decisions accordingly. And so if you don't get to your 20th goal, well that's okay, because I did everything I could. And I didn't sacrifice what mattered to me for things that didn't matter to me where people go wrong is they don't rank order them. They don't know what their priorities are. And it doesn't mean that hey, I'm always doing my first Priority, it just means that you have an awareness as to what matters most to you. So that in the end of the day, or the end of the week, or the end of the month or quarter a year, when you audit your focus and your time and your energy and your efforts, you then have to ask yourself, Am I living my values? Am I truly living my roles and my goals? And am I doing it in the order of priority that I set? And then if you're not, then you have to ask yourself, one of two things, either I set the wrong roles and priorities. I'm not being intellectually honest, myself, or I set the right ones, I'm not just doing what I really want to do. And then you sort of make those adjustments. And having that framework is really critical. Right?
Wanda Wallace 50:41
Right. It's interesting that you say the roles that you want to serve, because often people will talk about it. Well, Steve Freeman in particular talks about it, the people that matter most to you, and what those people are expecting from you. But I like this roles framework that you want to be clear the roles you want to serve, to want to be a team leader, to want to be a parent do I want to be, I don't know what whatever those are, that are important to you, and be honest about that. And then the prioritization, I think is essential. Because without that, you won't make the compromise trade offs you need to make.
Mike Rubin 51:16
That's, you know, that's 100% True. And in my experience, you know, you could set all sorts of goals for what you know, what you might want out of a specific relationship, or you might want out of a specific business enterprise or educational enterprise. But in the end analysis, it's it's really about the journey life is, is all a journey. And so if that's the case, then what journey you're on, to me is analogous to what roles you assume if you're on this journey of, of being a parent, or you're on this journey of being a spouse, you're on this journey of being an entrepreneur, and that's truly what fundamentally matters to you. Well, then you'll find yourself persevering. Because, yeah, you'll set goals, and sometimes you'll win. And sometimes you won't, that's inevitable for all of us as humans, but what you'll know, with certitude is, I'm on the journey I want to be on and that's you know, to answer the earlier question about how you know, when you when you persevere, is because you know what journeys matter to you, right, and you know, what your family means to you, you know, what your your career means to you, and you become less outcome oriented and more value and role oriented. And that really helps persevere and persist.
Wanda Wallace 52:31
Okay? All right. So if I try to wrap this conversation up in the one minute summary, I'm gonna say reframe risk, not by what you might fail at, but by what's the risk of not giving myself the shot. So that I open up what I really want to do, I got to figure out what I'm really passionate about. Because if I haven't figured that out, I'm going to have a hard time doing the things that I need to do. I've got to be prepared to ask the right questions, which is partly surrounding myself by some people who are very smart. But by showing up by understanding that passion by having the right conversations, and by focusing on what really, really matters, and then I gotta be willing to take the side door. So looking at the possible, the plausible, and the probable and various combinations of those, but being honest with myself about what I'm trying and what's working, get the feedback.
Wanda Wallace 53:19
But none of that works without some starting clarity, like rock solid clarity, on the values by which you want to live as a human being, the roles that you want to be part of or the journeys that you want to be on. I like that language and the goals that you want to achieve in the order in which you want to achieve them for all three of them. Because those guide the opportunities I'm giving myself, how many more times am I going to reiterate on this going before I pivot and do something else, they guide what I'm really passionate about? They got who I'm going to surround myself by the kind of guide everything at the end of the day. Very trail. All right, I love it. I love it. Okay, one minute super fast, what takes you out of your comfort zone?
Mike Rubin 54:08
Trying new things that I know I'm not skilled at, you know, I take vocal lessons, I take guitar lessons. I know I know, not to know know how to sing or know how to play the guitar. But these have been aspirations of of mine and, and I go for it and just allowing myself the opportunity to do new things and learn and struggle and fail and laugh at myself and have the humor along the way makes it you know, makes it all worth while for me. So I'm constantly learning. I'm constantly working to learn things that I don't traditionally know how to do and challenge myself. And I love being out of my my comfort zone. I live out of my comfort zone. So you know, this is this is right up my alley,
Wanda Wallace 55:02
I get that one I get that one and that there's so much value in learning something new any rate, but I love that you said allow myself the chance to fail and have the humor about it as well but going for things that I just want to know, because I'm never going to be great at it but I want to know about it. Alright. Wonderful conversation. Thank you so much. My guest today Mike Rubin. As you can tell, Mike does a ton of things but currently founder and CEO of North pond ventures which is a science driven venture capital firm. Mike, thank you for being here. Really great pleasure and I've loved the conversation. Love the point about the journey you want to be on and being really clear about the priorities of those journeys. To thank Mike,
Mike Rubin 55:43
thank you, Wanda. Such such a pleasure. enjoyed the conversation.
Wanda Wallace 55:46
Thank you and join us next week for another episode and getting out of your comfort zone. Thank you for joining us today. Tune in for another edition next week with Dr. Wanda Wallace on the voice America Business Channel. Reach outside your comfort zone this week.
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