This is part one of my interview with Brandon Bruce. Brandon grew up in a small California town of 800 people and had only one classmate in grade school. Seven years ago, he co-founded Cirrus Insight and has helped grow the company to $12m in annual revenue, 58 employees, and #41 on the Inc. 500 list of fastest-growing companies. Entrepreneurship looks different for each adventurer. His story is one of endurance and patience.
Cirrus Insight is a plugin for Gmail and Outlook for salespeople. It’s an all-in-one sales productivity platform with world-class Salesforce integration. 250,000 people use Cirrus Insight and its sister products Attach.io and Assistant.to to work faster and smarter from the inbox and calendar.
Brandon has also authored several books which you can find on Amazon. His most recent is called The Slow Sale: How Slowing Down Wins More Deals – which I highly recommend because it addresses the critical response that is necessary when entering the “quiet period” of engagement with your prospects. It’s an easy and practical read that I’m confident you will find helpful in evaluating your sales process.
Brandon loves endurance sports and raced his bicycle 508 miles across Death Valley in 2002 as part of the Furnace Creek 508. He finished in 35 hours and 7 minutes. He also enjoys hiking, camping, and building with Legos. Brandon lives in Knoxville with his wife, Tricia, and their two children, Sonoma and Carson.
Mark: 02:43 Brandon it’s a pleasure to have you here today. Welcome to the Leader to Leader podcast. I know that people are probably really anxious to get to know something about you that you never told anyone else or maybe you didn’t tell everyone about. So what’s something about you that people don’t know?
Brandon: 02:58 One of the things that a lot of people don’t know about me now, now that I’m an adult out in the work world, is that when I was in middle school, I was the spelling bee champion for Santa Barbara County. Why is that important now that I’m almost 40 years old because it’s actually one of my fondest memories and people don’t think of like studying for a spelling bee as being a super fun activity. But it’s one of the things when I look back, I mean, especially my mom and I, just sat for hours and hours and ran through the spelling bee questions right? To the point that you’ve got this big booklet of like 200-300 pages of words and you can spell all of them. So it was a great exercise. And just practicing and taking something seriously and getting it wired to the point where you could go in and knock out these words and it opened up this really cool opportunity to take a family trip.
Brandon: 03:44 We got to go to the state capital and go to the state spelling bee. And there were cool cartoonists there that drew custom pictures for you and everything. So now that my kids are little, they’re in elementary school now and I’m sort of looking forward a few years and thinking maybe there’ll be an opportunity to study some spelling words with them, a semicolon. We’re now in the age where everyone’s just tapping on their phones. Right? And there’s spell correct that everyone uses Siri, hey google. And so spelling kind of happens for you in a lot of cases. For me, I have such a good memory of it, I hope that they will be interested in doing it. And thankfully ESPN now runs the spelling bee contest. So people still are kind of fascinated by the whole idea of spelling.
Mark: 04:24 I’ve watched more than one spelling bee. So yeah, that’s really cool. And I think that element of competition that exists there, I mean there’s the element that exists for you as the individual always wanting, obviously to improve your skill, but also getting to compete against other kids and in some cases I suppose kids older than you as well, which is always an honor to beat somebody who’s older than you!
Brandon: 04:47 I went to a super small schools growing up. My grade school through fifth grade, I was in a class of two and then after that in middle school, it got substantially bigger. I was in a class of 15! That was cool to come back to this little tiny school and, you know, have a little trophy and be like, hey, check this out. So the whole school was really excited about it. So yeah, good. Good memories on all fronts. And, it was neat too. I’ve always been competitive in athletics. So it was fun to have, like you say, like, like a kind of a “scholarly” competition where you could kind of flex on the brain side of the house.
Mark: 05:22 That’s really interesting. And I think like business, life is full of these opposites or juxtaposition and the most obvious that I think exists oftentimes in businesses is this idea that you’ve got the sprint portion and you’ve got the marathon or the long-haul portion and both of them require different elements of training, but they’re both present and relevant in endurance sports. And I know that you’ve done bike racing across Death Valley. It certainly falls on the long haul or the marathon side, and you’ve also obviously had an interest in those sporting activities, but it led you also to boxing, which I thought was really kind of cool as well. It might be one of the best examples of pacing and endurance to experience success when maybe a knockout isn’t necessarily going to be able to be planned and it doesn’t always occur in the first minutes of the first round. So, in many ways, your book, The Slow Sale, takes that perspective into account by acknowledging that where you are in the sales cycle can often indicate whether you’re sprinting or in the marathon. What got you interested in endurance racing and boxing in the first place? Then how did it help you with business?
Brandon: 06:34 It’s funny to think back when I was a kid and think about some of the athletes that I really enjoyed watching and the fact that so many of them shared in common, the willingness to go the distance. So I played a lot of tennis when I was a kid and I remember really liking a whole range of players and in fact, Jimmy Connors lived in the small town where I grew up in. He trained there. So it was fun to watch him of course and I was a big fan. I also really enjoyed watching Ivan Lendl play and you know, there was a guy who was perfectly willing to go out and lose the first two sets. Like it was a warmup, right? Like get a couple hours into the match and then just wear his opponent down over five sets and win and do that several times in a row in order to win a tournament.
Brandon: 07:16 And you could see the other players would just, they just ran out of juice. And I thought, what an interesting strategy because tennis is very explosive. You can hit a bunch of aces and big serves and so there’s that sprint element, but there’s also this, hey, I’m willing to be out on the court for five, six hours if you are. So many of the opponents were not or they were not prepared to do it. So a lot of that just started to appeal to me later. I’m tall, I’m about 6’8″ and so I played some basketball as you might expect growing up and people would ask Hey, can we get you to come out and play a little bit because you’re pretty close to the hoop? So I played a little bit in college with the team and I would train with the players especially.
Brandon: 07:54 But what I started to realize was, and I enjoyed the game of basketball just fine, but I wouldn’t say I was passionate about the game itself. So I would play and then we would go out and do like hill sprints. And, what I started to realize is I was more excited about the hill sprints than I was about playing of the basketball, so I do like the first hour and a half of practice playing basketball and it was like oh, it’s hill sprint time and everyone else was like, oh man, like, this is going to be terrible. And I’d be like, this will be awesome. We get to go run the hills! So that sort of thing for some reason just made sense to me. I enjoy repetition. I got really into rowing in college, which to your point is there’s an explosive aspect.
Brandon: 08:30 You try to get all the team rowing with the exact same cadence and kind of jump off the blocks to get the lead. But then it’s really about endurance, right? How long can you do something repetitive, pull the oar through the water? Uh, essentially until you, throw up is, is the goal of rowing! So yeah, once I got into the sales business, when we started Cirrus Insight seven years ago to sell sales software to salespeople, I started to really give some thought to how sales works and I was very impatient, still am, um, but it was like, hey, if this person wants the software and I have the software to sell, let’s just go ahead and get the deal done. And so I would try to move the deal, you know, as quickly as I thought it could move, I thought, you know, in a respectful way.
Brandon: 09:11 But still I was always like, why, why isn’t it this closing like yesterday? And we had a series of, I think three opportunities very early in the life of the company. So I was the only person doing sales and my co-founder Ryan was the brilliant architect behind the app and was coding away. So I have these three and it was a big deal to move the needle of the company and all of them I felt like, you know, we had demoed the app, they have tried it. We had kind of negotiated around the contract, but the deals weren’t signed yet, and checks hadn’t come in yet. And so I was going to take my first kind of long weekend since we started the company, right?! We’re like six, nine months in the company, haven’t taken an hour off. And so my wife and I decided to take a long weekend and I was really worried that I was going to drop the ball on these.
Brandon: 09:52 Like what can I do? I need to be following up like every few hours, right?! And I’m driving these customers crazy and what I learned by stepping away and taking a little bit of time away from those deals and thankfully you know, good ending to the story. All three of them close, but I didn’t need to just harangue the customers in order to get them to agree to sign. They were on their time and they weren’t necessarily on the sales person’s time. And, that’s something that, you know, I still grapple with, I think weekly, monthly, with our sales team is we really try to spend concerted effort figuring out where are we on the map. It’s like one of those mall maps which has a red dot like You Are Here and you’re trying to get, you know, to the outlet store over here and you kind of need to know where you are.
Brandon: 10:35 And sometimes we say, Oh yeah, this opportunity, it was really rolling. And it’s like, yeah, but at least in our industry, have you done the security review? Have you talked with procurement yet? Has their legal looked at it and then has our legal, which is me, uh, looked at it yet? And if we can do all those things in parallel, we can advance the deal faster if we can’t, it’s going to take longer. But really knowing, we had to figure out over the last several years what those steps were, what order they generally need to go in. And then not rush the opportunity process too fast because it just simply can’t be. We’ve tried to do it before, we’ve tried to sprint, during the middle of an opportunity. It just doesn’t work. I mean, you’re talking about, nope, it’s going to take six weeks and it’s just going to take six weeks and it’s wrapping your mind around that so that you don’t chase the customer away.
Brandon: 11:22 And we’ve all had that experience, right? The “pushy salesperson” that you start to wonder, start to get worried, are they just in it for them? Is there something wrong? So they need me to buy right away? Is the company stable? All those sorts of things you start to worry about as a customer. Whereas if the salesperson has done their work and they’re respectful, then what we found, not only anecdotally, but we also looked at our data, and we started to see that there is what I’ve come to phrase “the quiet period.” So when we do all of our work, there’s been kind of a flurry of questions and answers between us and the customer. There’s usually a 10 day period where there’s absolutely no communication and then the contract gets signed. and it’s during those 10 days, that’s the most alarming to the salesperson because that quiet time also really looks like the customer has walked away. You don’t really know which has happened, so you wait for those 10 days and you get the signature and if you haven’t after the 10 days, then you can go into like little minor panic mode and try to figure out what’s happened, right? Did someone take a long vacation or are they out of the office or whatever. Otherwise, you kind of have to wait those 10 days. At least for our company in our industry, it’s that magic 10 days and that’s when the contract gets signed.
Mark: 12:30 It’s really interesting because it seems to introduce that concept of the need for rest which is an important part of training as well, right? So, you don’t typically like if you’re preparing to run a marathon, you don’t typically train every day and you certainly don’t train everyday at marathon distance and you’re varying the distances that you’re running and you know there might be this edginess inside of you as you’re preparing thinking, wow, you know, I haven’t even run the distance yet, but I feel like I really have got to so I get. I get that concept of needing to be content to let the process rest, let people breathe, let them do their due diligence on both ends and let it go into that quiet period, which is pretty disturbing. I think generally people are pretty uncomfortable with silence overall, but when you think about what’s required for endurance, mental or physical, one without the other obviously isn’t going to get you to the finish line. You have to have this combination of both. I’m sure that when you were building Cirrus Insight that it required both, but how did you make sure that you had what you needed in the tank to actually deliver on your own expectations? Maybe Ryan’s, and what were you trying to balance and how did you know when you had the right level of stamina that was required in either space.
Brandon: 13:54 Yeah. It was interesting and a couple thoughts come to mind. One is one of my favorite quotes about entrepreneurs is an entrepreneur is a person who works 80 hours so they don’t have to work 40. In a lot of ways, that was what I was looking for, where I could sink a lot of energy, a lot of time, a lot of effort into something. And so starting Cirrus Insight with Ryan, who’s been a friend for 20 years, we went to undergraduate together at UC Santa Barbara has been in a lot of ways a dream come true. It’s what I wanted to do. I wanted something where I could utilize, you know, hopefully a range of skills, some kind of a generalist. I’ve always felt like I can do a lot of things. I don’t necessarily have one area of expertise per se, but I feel like I’ve always had the capacity to work hard, so once we were able to start and that was the key, right?!
Brandon: 14:43 Starting is. It’s been a fun ride. I think my dad always said as we were growing up that if you ever have a problem that you really get stuck on, his advice was to go take a run, and he’s like, I almost guarantee that you’ll have the answer by the end of the run. Of course, then he followed that up with, if you don’t have the answer by the end of the run then keep running. You’ll figure it out eventually. And it’s interesting, right? There’s a lot of research and science behind getting outdoors, more oxygen in the system, positive endorphins, taking a step away from the work at hand to give your mind space to just think and you know, make these random connections that usually lead to breakthroughs when you’re trying to solve problems. So that’s been a big thing is trying to keep some sort of balance and my mom has said, and this has become more and more important to me that is thinking about kind of seasons of life.
Brandon: 15:40 So I’ve done some reading of books that talk about that recently, but I remember when we went to start the company, my mom had said, well this is an exciting time of your life because you get to do everything all at the same time. She’s like, you know, you’re married, you’re going to start a family. So my son was born the day after we launched the website for the company. So it was like, you’re going to start a family, you’re gonna raise your kids, you’re gonna start a company, you’re going to move, you know, you can get your first house. Like all of these things are happening all at the same time. Which on the one hand is kind of insane because you go, well I want to step by step all these things, but that’s just not the way it is. So you kind of try to leverage the energy and all the parts of my life, at least that’s what I’ve tried to do. So I’ve taken a lot of inspiration and enthusiasm and curiosity from, you know, watching and interacting with my kids, right?! They’re little and they’re excited and so it’s fun to kind of borrow some of their energy as we work on the company. And that’s been part of it.
Mark: 16:35 One of the things that you mentioned when you were talking about rowing is how you have to pace yourself and there’s that cadence and you don’t get too far out in front and you don’t allow yourself to fall too far behind the leaders. Are there dangers that you see that exist in focusing too much on competitors inside or outside of your industry? And can you think of an example where paying attention to competition brought benefit as well?
Brandon: 17:01 Yeah, I think especially early on in the life of the company when we saw competitors coming into our space, because we were the first mover, we’re the first application that connected Gmail with Salesforce, the customer relationship management platform. So we got out first and that was really helpful to be in the game and then when we started seeing competitors come in and some of them raised a lot of money, we were largely a bootstrap startup, kind of lightly funded with a few angel investors. That was alarming to us. The first time it happened where it was like someone’s coming in and they’ve raised eight figures of funding and we’re like, gulp, this is scary. We then came to get used to that as I go. Another competitor just came in, but when the first few happened, we spent, I would argue an inordinate amount of time focusing on, okay, now what are they going to do next?
Brandon: 17:43 What features are they going to roll out? How are they going to go to market? What sort of advertising are they doing? How big is their team now? Right? Or they’re using all that money to hire a lot of people. How are we going to compete? And it turned out after a couple folks had come to the market, we sort of said, well, all the time that we may spend focusing on what they’re doing is really time wasted. Like we were much better served spending that exact same time talking with our customers and making sure we were focused on delivering on the roadmap that they had asked us to do, the features that they wanted that would help them succeed in their marketplaces. That’s really remained our focus since. To your point, at the same time, we don’t want to be an ostrich with our head in the ground.
Brandon: 18:22 Hey, never mind what’s happening around us. You know, I’ve been lucky to be able to cultivate friendships, I think with most of the other founders and leaders and kind of our sales enablement space and I really enjoy. I mean, those are folks that I’ve learned a lot from because they’re in the same game. Everyone’s pursuing it slightly differently. Everyone’s got different sets of investors, different go to market strategies, different angles where they’re trying to serve customers. Yeah. Those are folks that I feel like I hope that I share a lot in common within the sense that we’re all, we’re all out there hustling and so it’s fun to see how other people approach it. Sometimes that’s surprising to people. They’ll be like, you talk with the CEO of this other, that you’re like head to head competitors and it’s like, yeah.
Brandon: 19:04 And as a result we share a ton in common, you know, it’s uh, there’s no reason that can’t be, you know, a cordial and a mutually beneficial friendship. You know, we’re not going to share each other’s code with each other. We’re not going to swap software, but we can talk about, hey, what are you seeing in the overall marketplace? How are customers reacting to these new features? This is stuff that’s not proprietary, but the sharing of information and help both of our companies grow. So net-net, when we see competitors or other people in our space growing, that’s actually turned out to be a really good sign versus a, hey, they’re growing, we would rather have taken that growth! If they’re growing, then we have our chance also. I think in some ways it goes back to the, you know, what, what’s, what’s the best place to put a gas station next to another gas station because people are stopping, so we want to be in the considered set as they say in marketing when people are going out to buy sales enablement tools, we want to be one of those applications that they say we need to look at this.
Brandon: 20:01 This is important.
Mark: 20:02 You Bet. Of course, I and there’s this element I suspect of having had to have done it maybe to really get it and there are some people who are listening today who are in various stages of their own startup. There are some who are already operating in a fully functioning business, but there obviously have been a lot of challenges and obstacles that you and Ryan faced at Cirrus Insight. As you got the business off the ground, you had to work to overcome, I suspect some fairly significant challenges. Are you able to describe some of the feelings that would lead you to question whether you should quit in the process and maybe those feelings that you experienced whenever you found success and the reward of having pressed through? Is it something that you can put into words?
Brandon: 20:54 Yeah, I think there were several occasions over the last seven years since the time we started the company where there were some legitimate existential threats, right? Where if something doesn’t go right or if the trend continues or doesn’t continue, that the business was really at risk. And so one of the great things and you kind of alluded to it is the fact that, uh, that I have a co-founder, Ryan, who’s also a really close friend. That I think has been really important and it’s interesting to read reports by different businesses and investor groups and so forth that really looked for teams of founders. And I think sure, there’s the complimentary skillsets, et cetera. But I think equally, if not, more importantly, it’s the fact that we can lean on each other. So it was a great interview with Warren Buffett years ago where I think it was in a classroom scenario and they asked him, Hey, what’s the trait that has enabled you to be the world’s greatest investor of all time?
Brandon: 21:47 And I think people were leading him down a path they expected him to say, you know, perseverance, the ability to take a risk intelligence to see opportunities and market and instead he surprised the audience by saying emotional stability. And when you back away from that and go, well, of course, he’s investing in a market. The market goes up and down and so you can’t necessarily predict all the things that are going to happen of course. And so, but if you’re stable. So because Ryan has been there if I have been super high on something and we’re, we’re killing it, we’ve got the right app at the right time or getting out to customers and we’re winning. Then all of a sudden then he can say, great, you know, let’s celebrate the win and then let’s get back to work. And at the same time, if I get really low, like, Oh man, you know, I lost that opportunity.
Brandon: 22:29 I thought I was going to win it. We’re not going to hit our number this month. Then you know, he can back me up and say it’s not that bad. This happened last year. And look where we are now. You know, we’re twice, three times bigger of a company. We’re more successful. We’ve got more customers, the customers are happier and I can do the same thing for him. So being able to keep a relatively even keel. Celebrating the wins certainly, and I think early on especially, we didn’t do that enough. It was really, we would get a win and it’s like, well we better just keep working. Like we don’t know when the next one’s going to come. So we better keep our head down. I think it’s good to take a, take a pause and celebrate the win. But it’s also important on the flip side to not take the losses as hard as, as I tend to do because of that competition and the impatience and the wanting to drive and the wanting to make things work.
Brandon: 23:12 That’s kind of my self-proclaimed role is like figuring out the go to market. We got a product, we like it, we know other people, how do I get it out there? And so when I’ve been stymied in that process, I get extremely frustrated. So being able to overcome that frustration and out there, you know, I don’t think there’s ever been a time since we started where I’ve said to your question, I don’t want to do that anymore. I want to quit. But there have been times where I felt like the business has been under threat. Right? So it’s like, I don’t want to quit, but I hope that this thing doesn’t happen because it could force me to. I watched a video, or you know, some of the books that I’ve read, but it was an exercise that takes you down a path that says what are all the things that could cause a business to fail?
Brandon: 23:56 And so usually you start this big brainstorming exercise like, well, you could run out of inventory, customers could pivot, you could lose product-market fit, a competitor could come in against you, you know, the market could get flooded with a commodity, et Cetera, et cetera. And you come up with this really long list of things. And then the moderator I think was basically saying, well, all those things may be true, but the one thing that causes a business to fail is you run out of money. And they just kind of bottom line the whole thing. And so yeah, the thing, the times that were really worrisome was an almost every entrepreneur I’ve talked with has said this. When people say, well, what keeps you up at night? If they answer with one word, it’s usually payroll because we have got to take care of the team. It’s the lifeblood of the business. And so early on there were some times where we really ran it tight right?! That break-even line as a bootstrap startup was a very, very close and those were kind of some nerve-wracking times. But yeah, we, we made it through that time period so that, uh, you know, hopefully, made us stronger and maybe a little bit smarter.
Mark: 24:57 Yeah, of course, we all know what’s going to happen if I crack up to the starting line of the Death Valley race and I’ve never done more than ride my bike around the neighborhood, if I recall correctly, I think that race was like more than 500 miles, 508 miles or something like that. Am I about right there?
Brandon: 25:15 Yes, the Furnace Creek 508 single-stage bicycle race across Death Valley.
Mark: 25:21 With a name like Furnace Creek, who wouldn’t look forward to it – just sounds awesome. So what do you tell someone who thinks that they want to start a business and maybe they don’t have any experience starting a business and you really don’t get any experience starting a business unless you participate? I mean how do they train or prepare for that? And I suspect that there may be are things that you would do differently in hindsight, but we’ll get to that in a second. I just want to think about like if I’m. If I’m going to say, well this is the path I want to go down and I’ve never done it before and I’m just trying to draw the analogy with how foolish it would be for me to think I could go run a marathon if I’ve never even run around the block or never done more than running around the block. How do you transition into the expectations, I guess, that are placed on you as you start your first business? It’s got to be a little tough.
Brandon: 26:17 At a threshold level wanting to do it is a good place to start, which is to say, yeah, I started reading books about entrepreneurs and their stories, especially in high school and through college and I just found them captivating. I love the stories. It’s like, wow, this person took this idea and ran with it and got it this far and then did this and started this other company whether they were for-profit startups, or social enterprises, big government initiatives, whatever the case may be. Just you know, a group of people or a person that took an idea from, you know, largely zero, right, acorn, all the way up. They had something they provided value and so I love those stories and so I had decided that was something that I wanted to do, which is to say I’ve also talked with plenty of people that are like, yeah, I don’t think I want to do that.
Brandon: 27:03 In which case, no reason to force it, you know, just because I’ve enjoyed it and it was something I wanted to do and a lot of other people enjoy and want to do it too. It doesn’t mean that everyone has to like it, just like not everyone will be super happy if they got dropped in the middle of death valley to do a bike ride. That for some reason when I read about that race I was like, that’s awesome. I totally want to do that. And at that time I didn’t have a bike. Uh, I didn’t have a road bike so I bought my first road bike and trained on it for a year and then went out to death valley and did that ride. So I did a lot of centuries, you know, double centuries, a lot of solo rides down the coast. This was when I lived in California just to get ready for it.
Brandon: 27:41 And someone kind of anecdotally said, well you can always ride twice as far as you’ve written. And I was like, well that doesn’t necessarily make any sense at all. But I was like, but that’s okay. I’ll sort of buy into it. So to get ready for the 508, I went out and did a solo ride of about 250 miles. And then I thought, well, good enough. I know I can go twice as far that. Yeah, you sort of choose what you want to buy into. So yeah, so I had a lot of training. I think it’s the same in business. You want to do a lot of training. The question is what is that training?
Well, there was a whole bunch of great stuff in this first of a two-part interview with Brandon. Here are a few things I picked up:
- be willing to go the distance, last longer than your competition
- you will have to train hard – the conditioning is important
- the customer isn’t working from the same time frame as the salesperson
- don’t try to sprint when you are in “the quiet period”
- identify where there is a need for rest
- if you have a problem you can’t solve, go for a run
- spend the time you would be worrying about your competition talking to customers and focus on delivering what they need
- a competitor doing well in your industry is good for your industry
- celebrate the wins, even the little ones
- don’t allow yourself to get too high or too low
- the one things that will cause a business to fail is running out of money
- remember, you can always go twice as far as you’ve come – maintain the stretch
The time with Brandon in Part One was awesome; however, I want to point your attention to one critical idea that he left us with. He said “You choose what you buy into.” You get to choose each and every day what limitation you put on your life. So, choose to remove them!
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