Cultivating Luck in Business Endeavors and Relationships

Brendan McAdams and Sean Murphy discuss cultivating luck in business endeavors and relationships.

Cultivating Luck in Business Endeavors and Relationships

I first met Brendan McAdams (@BrendanMcAdams) in August of 2020 when when he dropped by a Virtual Bootstrapper Breakfast. He is an experienced enterprise salesperson and author (see “Brendan McAdams on Sales Craft: Proven Tips to Elevate Your Sales“) We have collaborated on several projects including “Why is an Enterprise Sale So Complex?” What follows is conversation we had about cultivating luck both in audio and as a transcript condensed and edited for clarity.


cultivating luck allows you to avoid or survive hazardous situationsBrendan McAdams: Hi, this is Brendan McAdams and I’m here talking with Sean Murphy about cultivating luck. It’s an important topic for both salespeople and for entrepreneurs, so we’re going to spend the next 30 minutes talking about luck, and how sales people and entrepreneurs can cultivate it both in business and in life.

Sean, why don’t you jump in and start talking to us about what luck is.

Sean Murphy: I define luck as an unexpected or rare positive outcome. It can also happen when you are in a hazardous situation–where the most likely outcomes are bad, but you have a neutral or only mildly negative result. For example, if I were in a bad car crash but I walked away from it with only a few bruises or scrapes. And I would say that to the extent that the unexpected or positive outcome came as a result of a conversation, or an interaction with somebody else, or somebody presenting to you an opportunity, things that involve people, there are methods for cultivating luck. The second kind of luck, where you were in a hazardous situation where you didn’t have a bad outcome, sometimes leads people to take more risk or decrease their margin of safety further. And so another kind of luck you can cultivate is to recognize that you were, in fact, lucky and build more margin to avoid those situations in the future.

Brendan: I find this an interesting conversation. I am not interested in random luck, like buying a lottery ticket and somehow winning. But people will often attribute things to luck that I don’t think are luck. Rather, I think they are actually the confluence of many small acts. These scenarios interest me a great deal, which is why it is important to talk about it.

Luck is the Residue of Design

Sean: One form of luck is an intelligent bet that pays off. Branch Rickey observed that “luck is the residue of design.” I think he outlines the kind of luck that you and I are interested in: engaging in a pattern of behavior, which over time, yields positive outcomes or positive effects. In other words, they have a low downside and occasionally have substantial upside. Right. And I think you and I both believe that you can cultivate luck or certain kinds of luck.

“Things worthwhile generally don’t just happen. Luck is a fact, but should not be a factor. Good luck is what is left over after intelligence and effort have combined at their best. Negligence or indifference are usually reviewed from an unlucky seat. The law of cause and effect and causality both work the same with inexorable exactitude. Luck is the residue of design.”

Branch Rickey

Brendan: It’s fun to approach a great outcome or accomplishment from a forensic perspective. I like to walk back through the various things that happened along the way, try to figure out the things that caused that great outcome to happen.

From that, I consider how many were due to my actions or were under my control. Since we are talking about ‘good luck’ here, this approach tends to give me insight into creating better luck. In many cases, a good outcome is an accumulation of many small events. And when you analyze these events after the fact, you begin to see that many were under your control.

Sean: There are ways to avoid bad luck. You can learn to recognize and avoid dangerous or unsafe situations. Alternatively, you can use more care and add more margin for error if you need to operate in a hazardous environment. One bias you can develop after you were in a dangerous situation, but had a good outcome, is that you don’t take appropriate precautions next time to either build more margin in or avoid similar situations. Another way to prevent bad luck is to follow Chesterton’s advice about taking down a fence. Before you alter or remove an existing barrier or safeguard, talk to the people who installed it and make sure you understand what problems they were trying to prevent. Another rule of thumb I like is that traditions solve problems that we’ve forgotten we had. So it’s okay to change a tradition, but you should understand what led to the evolution of that tradition.

Brendan: That’s a good observation. That makes perfect sense.

Brendan’s Example: Reaching Out to John Doerr

Sean: You had some examples where you’ve taken direct action that led to a fortunate outcome?

Brendan: Yes, I am thinking of one in particular that led to a big career moment. I had a chance to go to work for Healtheon in the early dot com era. (Healtheon ultimately became WebMD.) Jim Clark from Netscape fame wanted to go after healthcare, so started Healtheon with some of the Silicon Graphics team, and I had an opportunity to interview there because I knew someone who was going to be VP of Sales.

One of the investors was John Doerr of Kleiner Perkins, who was already a legend in the Silicon Valley VC community. And it so happened that he had been interviewed for an article in… I think it was Fast Company, or might have been Wired… and I had just read it.

The article had his email address at the bottom, and for some strange reason, I felt compelled to email him and email him out of the blue and say, John, I’m interviewing for a job with one of your investment companies. I wanted to know if I could have a few minutes of your time and ask you a few questions.

I don’t know what possessed me to do that at the time. I don’t know where I had the arrogance to assume that somebody like John Doerr would take the time to even read an email of mine, let alone answer. But he did. And he responded back within a few hours, 12 hours, something like that, and had me work with his administrative assistant to set something up.

Sure enough, he spent 20 – 25 minutes with me on the phone, and that set into motion a whole series of new opportunities. I mean, as a result of that conversation I ended working for Healtheon, which was one of those fundamentally great career opportunities.

I suppose what I take away from that example, what benefited me there, or ‘the luck’ in that moment was that, for some reason, I chose to have a bias for action. I chose to do something rather than sit back and assume that fear might take over, that I might instead not do something for fear that I might jeopardize the opportunity I would have had at Healtheon. That making a mistake was better than trying to avoid making a mistake is the way I would look at it today. And it fundamentally changed my career trajectory in a way that I couldn’t have predicted at the time. And it actually solidified the idea that I could do that more often.

Sean: Sounds like it was a lopsided bet. At some level, Doerr was likely interested in somebody who might be an early salesperson for one of his portfolio firms. So he’s got a stake in your success. And the worst that happens is that his admin looks at your email and deletes it, and Doerr never sees it.

Brendan: Yeah. But I guess the risk was that, if I had gotten on the phone with him and he came to the conclusion that I was not up to the task, he might pick up the phone and call the folks at Healtheon and say, “Hey, don’t waste your time on this guy.” I was young. I had some experience and some success that I could point to, but it could easily have gone the other way.

Sean: But all of your fine qualities would have ultimately come to light.

Brendan: They’re not always readily apparent, unfortunately. My qualities, whatever they are, are pretty well hidden… They can take a certain amount of digging.

Sean’s Example: Starting the Bootstrappers Breakfasts

Sean's example of cultivating luck is starting the Bootstrappers BreakfastBrendan: How about you? When have you been lucky?

Sean: I have been trying to think of a good example. Back in 2006, I was going to entrepreneur events. Some were at night; many were in bars and were often just casual bullshit conversations. And some meetings were held early in the morning, where consultants were comparing notes and putting issues on the table.

And I thought, you know, we got to do something like this for entrepreneurs. So we started the Bootstrappers Breakfast. We’ve been meeting since October of 2006. And I met many entrepreneurs as a result. At this point, I have personally taken part in at least four hundred breakfasts and met several thousand entrepreneurs as a result.

In 2019 we started to offer one a month online, and then in 2020, COVID pushed us entirely online, but we are back to doing two a month face to face in Silicon Valley.

It allowed me to meet Dr. Alastair Hood when he came to Silicon Valley in 2008; I was immediately impressed. We have stayed in touch and collaborated on several projects. When Dr. Giacomo Vacca was leaving Abbott to start Kinetic River, he took part in a breakfast. That led to us collaborating on BeamWise. More recently, Scott Swaaley was encouraged by a fellow entrepreneur. He was starting MakeSafe Tools. He made several connections that have helped him move forward.

I am happy to have created something that provides value to the entrepreneur community, both bootstrappers starting out and serial entrepreneurs.

There are some subtleties in the design it took me a while to appreciate. For example, the round table discussion format allows people to meet many more people than they would at a presentation-oriented event. Most audience members at a presentation end up talking to only two or three others before or after the event. Also, it’s a more introvert-friendly format: you have a chance to hear other people speak and talk and problem solve before adding your perspective. So we get a lot more technical founders and co-founders join us.

I think it’s interesting that we both picked examples where we had agency and created opportunities. A critical part of making yourself luckier is to take action. It’s resisting the urge to sit there thinking, “Nothing I do will ever work. So I’m not even going to embarrass myself by trying.”

Brendan: That’s how you and I met as well, at a Bootstrappers Breakfast.

The other thing I would say is that you and I are not alone in this. I mean, most anybody listening, I’m sure they can look back at moments in their life when they did the same sort of thing. Where they took some action, and the outcome was successful, and they could probably map their way back to some small series of events that culminated in that win.

Look for Opportunities In a Setback

When you look for opportunities enabled by a setback you are cultivating luckSean: I think the more fundamental thing about increasing your luck is a mindset where you’re looking for opportunities even in a setback. When presented with a new opportunity, you become mindful of the risks before jumping in. I think it’s like looking both ways before you cross the street. What do you think are some critical aspects of your mindset that contribute to your luck?

Brendan: You touched on looking for opportunities and setbacks, which I view as taking an optimistic outlook on things. I like to think about how I can provide value in every interaction with people. How can I help them or contribute in a positive way? When I keep my default outlook on being helpful, I find it pays off more often than it doesn’t.

Every now and then I suppose I get burned or disappointed by the reaction I get. But most of the time, the overwhelming percentage of time, people respond favorably to that. And they tend to reciprocate, and that creates a positive outlook or a positive result. And I guess in some ways, that’s kind of a growth mindset that’s looking for a way of thinking about things in a positive sense, in an optimistic sense.

Another way to look at it is this. You have an ethical basis for your approach. You treat people fairly, treat people honestly. Over the long haul, that pays off.

Yes, it may not pay off instantly. In a specific example, it may benefit you over the short run to lie or be duplicitous. But in the long run, having an ethical stance and ethical approach to things makes you a reliable partner in business and life. And people are always on the lookout for reliable partners and reliable people to work with. Because over the long run, reliable people take less time and energy. So that tends to create more opportunity for a better outcome. Again, another way that you can cultivate conditions for better luck.

Sean: Ethics are important, certainly over the long run. You really get to know someone when you divide the profits from a joint win. And even more so when you experience a joint setback or loss. I think the temptation with a loss is to push the risk off of your plate onto the other party. If you can avoid that temptation and absorb your fair share of the risk or the downside, even though it’s a bad outcome, I think that not only do your partners remember that, but people who were only peripherally involved.

Brendan: Yeah, that’s the long-term growth mindset view of things, right? You have to decide that you’re taking a long-term view of things. And if you do that, I think that pays off reliably.

One of the things for me is, I’ve been in sales for a long time, and I’ve never really had a tremendous urge to take every dollar that’s on the table. It’s never been the sort of thing that motivated me about the sale, so I don’t feel like I have to get every dollar when I am negotiating a deal. I don’t feel like I have to beat the person that’s across the table.

Instead, I look for situations where I can create an environment where we end up on the same side of the table and we’re working through the problem together. It’s a growth mindset approach, I guess, that a rising tide floats all boats. And I think that attitude telegraphs itself. People figure that out. They recognize it if you have that philosophy, and if they see that, give you the benefit of the doubt, I think.

Sean: Your observation about the “benefit of the doubt” highlights another aspect of luck where opportunities are presented to you by others because they’re favorably disposed towards you. This may be due to past interactions directly with them, or it may be due to the reputation you have developed in a shared network or community. Reputation can also repel opportunity: people are less likely to bring you a new option if you must always have the biggest piece of any deal.

Another thing I try and do is connect people that would benefit from a conversation. For example, after facilitating the breakfasts for a year, I realized that I should introduce people who had come to different breakfasts who would have had a conversation if they had been at the same breakfast. That led to keeping more careful track of what others were looking for to move their business forward–and to try to determine what else would help them move forward.

What would you say are some strategies that you try and engage in consciously to increase the level of luck in your life and endeavors?

Brendan: Well, at one level, one of the things I look to do is surround myself with people who are optimistic. People who have that growth mindset, or see themselves as lucky. Because at some level, if you think you’re lucky, it delivers that outcome. And people want to be around that.

Another good strategy is this… I try to surround myself with people that are smarter than I am, because they elevate your game. They make you better. It’s one of the reasons why I’m friends with you. Engaging with you forces me to learn stuff. It broadens my perspective, and that generally provides new opportunities. Like this one. That has proven to be a really good strategy for me. Find people who are curious and smart, and not locked in to a certain idea perspective.

Sean: One of my business partners, Jeff Allison, was a senior manager and ultimately a VP of Engineering at Cisco. He had a rule that every project had to have one lucky person. At the time, I thought he was nuts. But now that I view luck as the ability to spot problems and opportunities early, maintain a positive outlook, and cultivate morale, I realize he was right. So I agree that finding smart people is a good idea. I think it’s also a good idea to keep track of folks who seem to uncover or create or design opportunities that weren’t there before they arrived.

Brendan: Exactly. I find it helpful to surround myself with people that are not too serious. They see, and maybe this is a kind of a corollary to optimism or intelligence, that there’s a certain absurdness to things.

Maybe this goes back to your whole idea of being able to overcome obstacles and operate past setbacks is that setbacks are often inevitable. And they oftentimes can be opportunities. And people that recognize there’s a certain randomness and a certain absurdness to life may be in a better position to respond effectively. That seems to me an invaluable skill or, you know, the right perspective to have.

Sean: I think playfulness may be a marker for design thinking and creativity. But I know that you would agree that if you make a commitment to somebody, you don’t come back a week later and go, “Hey, I was just kidding.” When you are walking around a problem and asking “what if?” playfulness is very helpful, but commitments need to be made intentionally and taken seriously.

Brendan: Yeah. But you’re right. And, you know, we’re still talking about the sort of characteristics you want to have in the people around you. And in yourself.

Yeah, commitment to deliver on an obligation, or when you do something you say you’re going to do. Now I’m thinking about it very specifically from a sales standpoint. It is tremendously impactful.

It’s an incredibly invaluable characteristic to have, to be consistent with customers in the sense that if you leave them with the expectation that you’re going to do something, then you need to figure out a way to do it.

People that make commitments, and then adhere to them, are ‘luckier.’ Not make them indiscriminately, but make commitments where you should, and then follow up on them. And I think those people tend to be luckier.

Sean: There’s something to that. I worked with a very talented Vietnamese guy, Hung Luu, on several design projects in the semiconductor industry. At one point, we were looking at some test results for an experiment we had run, and I said, “That can’t be right, that you must be mistaken.” He gave me a very disappointed look and said, “When I tell you that I’ve checked something, I’ve checked it. We have a problem.” So that reset my attitude: I realized I had been too cavalier and fundamentally demeaning. Not intentionally but unthinkingly. If you respect other people when they bring you bad news, they’re more likely to bring you bad news quickly. And the sooner you get bad news, the sooner you’re able to react and start addressing it. What are your ideas for how people can improve their luck?

Brendan: Well, there are a number of things that come to mind. I mean, there are a lot of simple little things. There are process or habit things that you should consider.

Think of them as tactics. I’m a sales guy. And so I think in terms of sales fundamentals. Things that emphasize reliability, for example. Like showing up on time, being on time or early, being reliable creates a level of comfort for customers.

It’s no different than a train or bus showing up on time. Having someone that shows up, someone that’s reliable and that they can bank on is an asset.

Another one… you talked about making connections and making introductions. I do the same. That happens to be a really effective way to give back, give to get, to contribute.

How about you? What things can you suggest?


When you smile you are cultivating luckSean: I suffer from a condition that I need to manage on an ongoing basis, especially when meeting new people. The layman’s term for it is “bitchy resting face” complicated by ”‘cranky old fart” syndrome. I have to force myself to smile and engage in a warm and friendly manner when meeting a new person. This helps me to overcome my natural inclination to give them a good hard stare, and look them over to see if they’re really going to be worth my time and trouble.

Brendan: Can I jump in on that? Yeah, that one fascinates me because I totally get that. I’m generally a happy guy. But the biological connection there is remarkable. The fact that smiling changes your mental state in an electrochemical way in the brain. It just fascinates the hell out of me that something as simple and as mundane as smiling can actually change your outcome because it changes brain chemistry and thus your mental state. That’s remarkable to me.

Sean: Effective entrepreneurs keep one foot in reality and one probing an imaginary landscape. Sometimes they jump into a dream with both feet and lose sight of what’s under their control. One way to increase your influence is to consider the communities, groups, and teams you’re a member of and see if you can help them become more healthy, more robust, and more successful. Despite the claims in many popular success stories, no one succeeds purely on their own. You carry many people with you, and many people–often different people–support you in turn. I think this goes back to your teams of Optimists or at least surround yourself about absolutely,

Brendan: Yes. I find there’s no payoff in taking credit for things. It doesn’t help to take credit. It’s much better to recognize other people. And this goes back to you know, having gratitude, but also the act of recognizing the contributions of others has a much greater impact on your future luck than taking credit for something that you did. if you did something that’s really remarkable, other people will typically figure it out without your help. No need to spend energy on that.

Sean: When you’re trying something new, you have to anticipate that things will go wrong. Gerald Weinberg observed, “Nothing new ever works.” One way to increase your luck is to plan for several iterations to get something innovative to get off to a good start. We are impressed if a baseball player gets a hit 30% of the times they step up to the plate–if they bat .300. So I think a 30% success rate is a good target for innovation efforts.

You have to give yourself options to recover from setbacks: don’t invest all of your effort, resources, and timeline on your first try. Plan on three at-bats to make it happen. Learn and adjust as you go. I see too many teams burn up all their resources on their first try. They come close. They achieve a result that is effectively a proof of concept, but they need to make some critical improvements to make it acceptable even to early adopters. Unfortunately, they are out of resources. You should plan for three tries, refining and improving as you go.

Brendan: For me, it’s at least three tries…

I have one more. And that is… hard work. Figure out how to enjoy the work. My father has a phrase. It goes like this: “Life’s a crap sandwich. Sometimes you get more bread, sometimes you get more crap, but you gotta eat the whole thing.” And it just says so much about my dad and his outlook on things.

My variation on that is this: “You have to learn to love the grind.” I say this all the time. If you find that you like the work, I think everything gets easier. And when things get easier, you get luckier.

This may be obvious, but just the idea that if you can get into liking the work and not focus on the reward or the outcome, that’s the secret. Scott Adams talks about how goals are pointless, and that everything is process. And if you can learn to love the grind or the process, everything else gets easier. Again, I think you get luckier.

Sean: I like your “show up early.” Thirty years ago, I worked with a guy who advised me, “I will tell you what my old boss told me: it’s ok if you can’t be on time. Just be early.”

Brendan: Yeah, that’s a good way to look at it.

Ultimately luck isn’t because of one thing. It’s a lot of little ingredients. It’s like bouillabaisse, right? It’s not one thing. It’s not just the bulb of fennel. It’s not just the tomato sauce. It’s not just the shrimp. It’s all the things together that make it work. That’s how you get luckier.

I don’t know if that metaphor works or not. But that’s what I’m going with. How’s that?

Sean: That’s good. You can increase certain kinds of luck. Luck increases with more activity, taking more intelligent risks, and developing expertise. Cultivating luck requires you to recognize and learn from your past mistakes and success so that you’re better able to spot potential problems and emerging opportunities. You can learn to love the grind if you take on work that incorporates some of your interests. I’m not saying you should make any of your hobbies into a business, but to the extent that you can leverage one or more of your interests to what you’re doing, you get luckier.

Brendan: Agreed! It builds on itself. I’m not sure we’ve exhausted the topic, but I think we’ve given it a good initial treatment. It’s fun to think through this stuff and try to break it down into its component parts. So, I think that’s where we’ll leave it. Thanks, Sean. This was fun.

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