Built for Uncertainty: Entrepreneurship, Failure, and Productive Tension

In this episode of Leadership Quotient, Lindsay Guzowski, CEO of The Crucible, speaks with Rishad Usmani, physician, angel investor, and serial entrepreneur, about the realities of building companies in environments where outcomes are uncertain and success is never guaranteed. Drawing from his experiences as both a practicing physician and startup founder, Rishad explores the fundamental differences between medicine and entrepreneurship, including the role of risk tolerance, failure, and decision-making under ambiguity. The conversation examines what founders often get wrong when building teams, why hiring should be a deliberate and rigorous process, and how complementary skill sets create stronger organizations than groups of like-minded individuals. Rishad also shares lessons from angel investing, explaining why founder quality increasingly outweighs product, market, or pitch deck considerations in his investment decisions. Throughout the discussion, he emphasizes the importance of curiosity, humility, productive tension, and building cultures where disagreement strengthens decision-making rather than undermines it.

Transcript

SPEAKER_01 0:00

Welcome to Leadership Quotient, a podcast by The Crucible, where we explore how leadership teams and investor-backed companies are built, aligned, and scaled for impact. I'm your host, Lindsay Gazowski, and in each episode, we'll talk with the people shaping value behind the scenes, from operating partners to investors to advisors to C-suite executives, about what it really takes to drive performance through leadership. On today's episode of the Leadership Quotient Podcast, I chat with Rashad Usmani, physician, angel investor, and serial entrepreneur about outcomes not being defined in entrepreneurship, selling three months ahead of your product, and why tension is positive. Rashad, welcome to Leadership Quotient. Your background is unique and different from a lot of people who find themselves in the venture in angel and early stage development space because you started in medicine. So how does one go from being a doctor to being a business builder and angel syndicate lead?

SPEAKER_00 1:19

Yeah, happy to share my story. I think for me uh personally, I'm not sure if I was meant to be uh strictly a physician. Um once I was uh had gone through residency and med school and everything, and was a practicing physician. I always was annoyed by all the inefficiencies in healthcare. So the, you know, there's a few things you can do when you're annoyed by something. You can you can complain uh or you can try and fix it. Um I was so annoyed that I was like, okay, I have to fix the these inefficiencies, and that would led to the start of my first startup, Clinic Up, which was to automate these inefficiencies. Um, we can get into that down the road, but essentially lots of lessons learned, uh, mostly about hiring, uh building a team, and kind of going back to the investing framework, which is, you know, that is the most important thing by far. Um, after I closed Clinic Up, I wanted to stay involved in the innovation ecosystem and in the healthcare ecosystem. And I thought, you know, that there's two ways I can do this. I can either do another startup, which I did not have the mental uh bandwidth to do so, um, or I can start investing in startups. I stayed involved in clinical medicine throughout even now. I'm I spend a couple days uh in clinical medicine a week. Uh sometimes more, sometimes less, but on average I'd say. Um so that that's how I got started into um investing. Um, is is I thought, okay, like let me start writing some angel checks. Um happy to get into specifics there, but essentially it on LinkedIn I went, okay, I'm I'm an angel investor in my title, and the floodgates opened. Um, and that that's how I got started. Yeah.

SPEAKER_01 3:08

And so talk to me a little bit about what skills you see as making a great physician. What's the orientation and personality background there? Then I'm going to contrast that with what makes a great founder.

SPEAKER_00 3:21

Yeah, and uh, I think I'll get some flack from my colleagues here. Uh but uh but a great physician is the anti-entrepreneur. Um, it's the in-the-box thinker to an extent. Um it's we're told these are the milestones you need to meet, and this is the outcome. It's a very defined path um to becoming an attending physician. So I think a great physician is someone who can see, okay, these are the problems I need to solve, and this is what will happen if I solve them. Um yeah, I'll I'll pause there and I'll kind of I'm leading into your next question, but I'll pause there.

SPEAKER_01 3:59

Sure. Um and for full transparency, my husband's a surgeon, and so I I think that resonates that it's there is a lot of problem solving, but it's problem solving within a sphere and making sure that you're minimizing risk and optimizing outcome as well as patient throughput. Um what skills did you need to build and or that were distinct when you approached becoming a founder and leading Clinic Up?

SPEAKER_00 4:35

So um Clinic Up, I made a lot of mistakes. I think I'm better in my current roles now. Um the biggest thing is when you do things you're supposed to do, the outcome is not defined. Um there's a lot of uh things that can go wrong um that you don't lead to that so you don't get the desired outcome for a startup, be it closing a business partnership or a key hire you wanted to make. So a lot of um the way you need to operate in a startup is um uh figure out what needs to be done, but constantly learn and use external signals that is this working, is this not working? And those signals aren't very defined. Um there's a lot more uncertainty in being a founder and leading a team. Um, and there are a lot of things you cannot plan for, but you still have to deal with them and you still have to figure out a way to keep going. Um and that there's a contrast there in clinical medicine is you know, sometimes things happen that you don't expect. Um but you have very defined pathways generally of dealing with things, um and these pathways don't really exist in in startups. Um yeah, and and you and you can't um you know the we're we're getting more into kind of maybe the the the subjective part of things, um but but the I think what makes a great founder um is someone who's curious, intelligent, and and persistent. And I think a lot of other people have probably said these things. Um but just curiosity about you know, why did this work? Why does this not work? Um, and then how can I do better next time and then just keep moving forward in in that instance. Um there's there's some parallels there in clinical leadership and in sorry in in being a physician and a clinician, but I I feel like the outcomes are a lot more defined there.

SPEAKER_01 6:40

Yeah, I think every med school in North America would say we're looking for curious, intelligent, persistent individuals, and that that's what's going to make a great doctor. So I'm I'm interested in understanding it's not just the outcomes being less defined, but are there inherent pieces that drive people into that entrepreneurial mindset that maybe doesn't exist in medicine, or is it a better training ground than people would think?

SPEAKER_00 7:13

I think risk tolerance is one of those things and um comfortable with failure. Um to grow a startup, you have to fail. Yeah. If you're not failing, I would say at least 20% of the time, it you're not succeeding, um, which is not the mantra in medicine, right? If if you get 100% in all your grades, if all your cases go amazingly well for your um surgeon husband, if nothing ever goes wrong in any surgery, that that's a clean record. That's something to be proud of. And that will lead to more success in medicine and maybe you know that that's defined as something to look look um to look up to. Um and it starts with being um not being tolerant of daily failures and then failures over weeks and months and years. Um in startups, if you will only do things where there's a guaranteed chance of success, you will essentially do nothing. Right. So the biggest hurdle I find um physician entrepreneurs um get into is they use the same framework as to, okay, I need to know all the information before I begin, or um I need to guarantee success before I begin. I need to have a high pretest probability for the clinicians listening of this test showing what I'm looking for.

unknown 8:36

Right?

SPEAKER_00 8:36

So in medicine for the non-physicians listening, there's something called pretest probability, which is why we don't order tests um, quote unquote willy-nilly. We are always thinking this is what this is the disease or this is the pathology I'm looking for, and then we order a test. Um and in startups, that pretest probability is it's undefined. Um you're kind of wanting to build a product that users love and figure out a business model um that can grow in scale. Um, to keep it very simple. But you know, in medicine, you have a pretest probability for every single thing. Someone comes in with me for a cough, like I have a pretest probability for anywhere from the common cold to lung cancer. And the more input I get, the probability goes up and down. I'm like, okay, do I need to order a chest x-ray or a CAT scan, or do I just need to wait? Um that doesn't exist in a startup, right? The pretest probability of me getting this selling into this insurance company with this contract is that there's so many more human factors. Um, a lot of it is dependent on your relationship with the people making the decisions, yeah. Um, as opposed to the product or the even the outcomes that your studies show. Um, those things matter, but your the the soft skills matter a lot more in entrepreneurship than they do in medicine.

SPEAKER_01 9:56

Fair points. So you mentioned that you made a lot of mistakes in building your first company. Talk to me a little bit about that from a leadership and team perspective.

SPEAKER_00 10:09

I think the the biggest mistakes I found is making the biggest mistake I made is I didn't take my time hiring. I kind of looked at who good who which candidates look better on their resume, you know, who had the um the meta logo or the Google logo or um who worked at this Mayo Clinic. And then I kind of went and chased those things. Um what you want is to spend hiring should be a painful process, right? If you're having fun hiring candidates, I think you're probably not doing it the right way. Um it should be very detail-oriented. Um, you should always do reference checks, at least two for every candidate. Um you know, but the the biggest um lesson that I took away was to take my time hiring and not to rush into hiring people. Um, and then the flip side of that is when someone is not working out is to fire fast. Right. I think in a bigger organization, you can afford to give people second chances. In a startup, you cannot. Um and maybe that's not the right way to think on a bigger scale, but at when you're a team of three um and one person is not working out, you need to let that person go right away.

SPEAKER_01 11:24

When you were thinking about constructing your team, it sounds like you were looking at individuals, not at the team dynamic as a whole. How do you advise your the founders that you work with or in your current startups, how are you thinking about creating that team dynamic?

SPEAKER_00 11:43

I think you hire people who are, you know, and this is maybe a cop-out answer a little bit, is hire people who are intelligent, curious, and and have humility. Um, and in my experience, if you do that, team dynamics sort of play out. Um, and as long as everyone's aligned um at what you're building towards and the goal, um, it works out. I think the one thing you have to watch out for is don't hire people with um with parallel skills. So everyone's skills um should be separate, um, should complement each other. So I'll speak with my current startup mana. Um so I'm more the the clinical person and the strategy lead. Um Jay um's back nice from Amazon, and she is marketing and product, and Patrick is the technical lead. Um, sometimes, you know, one of us will be like, okay, you know, I want to try this, and then it's kind of my job to be like, no, like this this is your strength. This is how you add the most value to the team. And I'm happy for people to learn adjacent skills and and um and verticals and and you know grow, um, but not at the very beginning. I think when we're a bigger company, then there's room for that. But there's so much work to be done as a startup. It's it's important to work together, but it's also important to have very defined roles everyone is doing, so you're not stepping on each other's toes. Um, I think duplication of work done is is very dangerous in a startup. Um because it it can easily stagnate, and then you're left with the decision, okay, well, whose paths should we choose? Um, so you need to have one decision maker, um, and then you need to have a team of people who know exactly what they're responsible for. Um and then everyone else needs to get out of their way. Um and that's not to say that they shouldn't give them feedback, but um but it it's their um it's their vertical, it's their lane, um so to say.

SPEAKER_01 13:43

Um so do you use any type of assessment as you're building the team?

SPEAKER_00 13:52

Um no, like um yeah, in terms of like Myers Briggs and personality tests and things like that, I don't.

SPEAKER_01 14:00

And selfish lab to say, you know, hopefully that as people are are using assessments or using statistically valid ones. Um that's the Myers-Briggs, it's a fun test, but you know, it so are horoscopes.

SPEAKER_00 14:13

Yeah, I I think people are using horoscopes and Myers-Briggs and not the I think it's called the big five is the um more uh more valid one. Um the the one thing I will do, uh, and and another VC told me this, Owen from Opal Ventures. Uh he goes line by line on someone's resume um and and starts at the very beginning. Um and you just want to the the main thing you're looking for is is this person honest and transparent? Um because we all have fillers in our resume. You know, I have a publication in the American Heart Journal and the Cardiology Journal as a glorified data entry clerk. Um, but I'm like fourth out there on the paper, right? So is this person being honest about their work and what they've done? Um and again, you you you want, you know, the I'm trying to find like a nice way to say this, but you want to tire the person out in the interview. Um you want to go deeper, you want to see how they perform when they're tired under pressure. Um, and some of that just comes from just asking them a lot of questions and just listening. Right. Um, so I do put my transcripts into Claude now and ask it, you know, how does this call go? What could I have done better? Um and so and I'm learning that way as well. I think that's probably a skill founders can use as well.

SPEAKER_01 15:38

Good. Yeah, the reason I ask is that as you were talking about team dynamics, it sounds like you had a very consistent set of orientations. And what we've seen from the crucible um is that often there are phenomenal people who exhibit a lot of the right skills, but don't have the same orientation toward how they process information, or that there's too much clustering around certain personality types without having a spread to create, you know, productive discord. Um and with that, just understanding whether you guys were engaged in some of that, some of that investigation, or if, well, frankly, your process got people that naturally had a similar orientation in the right ways that could then push forward because you're then able to get out of their way and share information as needed.

SPEAKER_00 16:30

So for for my startup, what I was looking for is a balance of uh user experience and clinical validation. So I want half the team to be fully focused on marketing, distribution, um, branding, and user experience and how our solution makes the user feel and makes our patients feel.

SPEAKER_01 16:50

Yeah.

SPEAKER_00 16:50

I want the other half of the team to be fully focused on is this technically sound, is this clinically valid, is does it meet regulatory master, what's the liability, what's the malpractice? And those are opposite sides of the same coin, I think. Um, and you have to build that balance in the founding team and maintain it as you hire. So as the team grows, like that is my North Star in terms of growing the team. Um, and the moment I have too many people who are more uh my natural inclination will be to have too many people on the clinical side, being a physician myself and being surrounded by physicians. Um so what I have to do, and what I'm doing is okay, I have way too many people who are telling me what the regulation is and what, and not enough people telling me what the branding is and how this app makes people feel. Like, you know, can we be the the Nike to someone's Reebok or whatever, right? And the Canology one or the Apple to someone's Microsoft. Um and and I think distribution is more important than the product. And this is something physicians just don't either we don't understand or we just don't accept, or we refuse to accept for whatever reason. Um but that that's one of the biggest lessons I've learned. So when I build a team, I want half the team to know that um and really be like distribution, distribution, distribution, and they have to be like, no, like we have to be clinically sound. And that tension needs to exist, and I need to be able to hold that tension and and keep moving the company forward.

SPEAKER_01 18:22

Good. So tell me about your experience in looking at other founder-led startups and some of the things you see that people are not doing to the level that they should be when you're thinking about leadership, team building, and construction of a future state organization.

SPEAKER_00 18:45

I think just people don't think about it, right? There's the founders I find who are um maybe having trouble here, they just they didn't think about their team before they started hiring, um, or they hire the first candidate that kind of fits the bill. Um, they don't do reference checks. Um and they just don't spend time. Okay, is my startup looking to sound like me? Um is no one giving a conflicting opinion? Um, are we all agreeing with each other? These are all signs that you're in trouble, I think. Um I think I think those are kind of the main ones, but you just have to kind of sit and just think about you know what what does it take to build a great startup? Uh and tension is good. Um so you know, we had a meeting uh and then we we have a deliverable in a in a month um that we're not prepared for. Um attention is is is important in a startup. You should sell, I would say, three months ahead of your product. So don't sell the product you have, sell the product you're building to an extent, but not a year ahead, right? Right. So I I think um and and this is how you kind of build the culture uh of your um startup. Is if if I just say, okay, we had a meeting, this is what this big player wants. Um the culture is built, okay. Let's build it, right? So I think the culture is built by doing, not what your manifesto says or what's on the walls in your office or on your website. Um yeah, so I mean I I think you know, know that the the culture is built by doing, not what you say. Like what you say is more or less irrelevant, it's what you do. Um and then spend your time hiring. Just just take your time. It's not a fast process. Um, I, you know, I went over 600 resumes, I talked to about uh 60 people for an hour long each before I made my hires, um, did reference checks. So just spend the time, right? And then that's if you talk to 60 people for your product manager role that you're hiring, then you know what a good product manager looks like because you've talked to 60 of them.

SPEAKER_01 21:03

Makes sense. So when you're writing an angel check, what are the the most important features that you're trying to see in that business or that founder?

SPEAKER_00 21:16

You know, I'm constantly changing my mind here. So I've done kind of the mistake of writing checks for um an amazing product in a growing market, but I wasn't too sure about the team. Versus I've skipped on checks for an amazing founder um in a market or the product I just don't think they could sell in that market. And I've been wrong. Um so now to be frank with you, I'm almost leaning towards I don't even know if a pitch deck business plan, marketing product matters. Um I think it's all about the founder. Um, you know, you have to kind of you need to look at their incorporation. Documents captable just to make sure they're honest and not lying. Sure. But if you if it's a trustworthy founder building a company they want to build, you have conviction they're going to stay loyal and keep building it, you back them up. Right. I don't know if anything else matters. It's easier for me to kind of do to see if it's a trustworthy founder that knows what they're doing, that are intelligent, that are curious in healthcare just because it's an industry I know. But as an investor, if you have a good eye for um people, right, I think I think that that's the most important thing.

SPEAKER_01 22:43

Great. And as we get into this current and future wave of value creation in companies that seems to be more and more tech enabled, how do you think those skills from a leadership perspective are going to change and evolve?

SPEAKER_00 23:03

I think we're going to have much smaller teams. I think it will be very common for the CEO to know everyone in a billion-dollar company, if not more. Um so, you know, the the role of managers will be interesting if it will exist at all. Um I think as a previously, as a CEO, you your role was initially to grow the company, but then to bring on people and train them to manage people under them. Right. I I don't think that role will exist in startups. Um, I'm sure it'll continue existing in incumbents and companies already there. Um so as a CEO, you have to be in charge of the ship um and lead people maybe in a more of a uh in a flat hierarchical structure, then maybe um our our current um training doesn't provide us the tools to do so.

SPEAKER_01 24:05

And that wraps up another inspiring episode of Leadership Quotient. Thank you to Rashad for taking the time to share his judgment and point of view. To our listeners, if you found this conversation valuable, be sure to subscribe to Leadership Quotient wherever you get your podcasts. You can also learn more about the Crucible and how we're helping investor-backed companies align leadership teams for scale at the crucible.com. We'll see you next time for more real conversations on leadership, talent, and value creation.