This is part two of my interview with Brandon Bruce. Here’s the link so you can go listen to Part One if you missed it: LTL 078: Endurance, Entrepreneurship, And Patience: An Interview With Brandon Bruce Part One.
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.
We finished Part One with Brandon’s thoughts on training and figuring out that you can always go twice as far as you have gone. He ended that part of the interview with this critical idea: he said, “you choose what you buy into”. Is that not just SO powerful?! You choose.
Brandon is WAY too modest. He mentions that he’s training for a bike ride fundraiser for Alzheimer’s research around the 17-minute mark of the recording. Well, he’s actually part of a 12-member team called the Summitt Cyclists who are each riding 1,098 miles between October 7 and October 17, 2018, from Knoxville, TN to Daytona Beach, FL!
Brandon: 2:10 So I live in Knoxville, Tennessee. I’m on the Board of the Knoxville Entrepreneur Center and we do a lot of work with folks that are interested in starting a business to say, okay, what are the things that we can do, you know, and a lot of it is just building excitement so that we can get ourselves over the hump of deciding to make that fateful decision to start.
Brandon: 2:28 And that’s the best decision Ryan and I made was to simply launch the application. And we talked about should we launch it now or should we stick to this really exciting roadmap that we have where we could knock out these features in like six months and the app would just be awesome, right? We’d be super happy about it. But then we had customers thankfully telling us, well, if you launch now we would pay for it, it has value to us, and we’re like, well shoot, we should honor that – we should launch. I’m so glad we did because we were first to market and it got us that first cohort of customers in seven years. It was the best decision we made was simply to launch. So we try to do a lot of encouragement at the Entrepreneur Center like hey, people are interested and they think they have an idea, they want to go.
Brandon: 3:04 Then launch and then I think thankfully, and this is probably true nationwide and globally over the last several years, there’s been a lot more backfill if you will, of programming information like so you decided to launch now what? Because I think at least at the time when we launched the company, I felt like there was a bit of a gap in the entrepreneurship market, if you will, where it’s like there’s a lot of enthusiasm for getting people to launch. But then if you did launch it was like, well, good luck to you, you know, you made the decision, we didn’t force you to do that, but now that you’re in, you’ve got to figure out all of it. Now there’s so many great growth academies and hacking schools and everything else to really create frameworks and you have examples of these companies that have done amazing things where you can learn from the people that built Airbnb and Uber and whatever and just try to draw on their wisdom and choose, you know, one or two things that they’ve done and try it out and see if it works in our business and that that’s what we’ve tried to do is learn from some of the people that are really All-Stars in the space and try to see if we can’t pull off half of one thing that they did that will help us to scale our business.
Brandon: 4:11 So yeah, it’s being curious. It’s being a student of it, I think because at the end of the, you know, someone told me once, at the end of the day you’ve got to be the expert in your business. You can’t start it and then go around to other people and be like, Hey, can you tell me what’s happening in my business? Can you help me to run it? Can you help explain my industry to me? Like you have pretty much got to be the expert in your own, in your own business, in your own industry and be able to run it and that requires, I think just a really high level of curiosity to want to keep studying it over and over again and seeing what’s happening, how the moving parts work together. As we talk about that a lot internally at the company is staying curious. Curiosity I think is a great antidote for lots of things that most of us want to avoid.
Brandon: 4:52 Namely getting stale and you burn out when you just do the same thing over and over again. You are hustling, hustling, hustling. Then you run out of juice. But if you’re curious, you’re like, gosh, I wonder if I can help this customer more. I wonder if I can solve their trouble ticket. I wonder if we can make the app work so that it will satisfy their sales workflow and make their team more efficient. As long as you keep that curiosity, you kind of want to see what’s on the other side each day, each week, each month keeps driving you forward.
Mark: 5:16 You’ve said a couple of things that I think we’re pretty interesting as I was preparing for our conversation. You did an interview on Mixergy awhile back and you talked about something that I thought was really important. You alluded to it a little bit in The Slow Sale as well. You talked about what I think is an oversight maybe in the excitement over getting started. You talked about the amount of time that you spent talking to customers and actually making sure that there was not only an interest but a need and a willingness to pay as you mentioned, a willingness to pay for the product. And then when you and Ryan decided, look, we’re gonna launch. You actually had people who were ready with their checkbook open to actually write you the proverbial check and get started with you.
Mark: 6:08 That seems to be something that is missed sometimes in the entrepreneurial effort and I know that you guys were working in the industry, and you had some insight because of your own frustrations with working between a CRM, a customer relationship management system, and an email client, where maybe you were doing a lot of engagement with customers, but I expect that even as time has gone on and you thought you really understood that space really well, that you probably came to a better understanding of your customer the more and more time that you spent with them. Does that ever go away?
Brandon: 6:46 I don’t think it does. And what’s interesting is, and so yeah, my advice to entrepreneurs when we’re hanging out, sometimes we’re all tempted to do this and we’ve done this in our own company and I looked back and I go, why, why did we do this? But we go into the lab and cook something up that we think is awesome and do it in secret because we want it to be this big surprise because who doesn’t like a great surprise party? You go in the lab, big surprise, you don’t tell anybody about it. And then you come out and you go ta da, you know, this is my gift to the market! And that can work. We’ve all seen at work and when it does, it’s incredible. But I think my fear is that it doesn’t work as often as we all would like. We would like it to work all the time.
Brandon: 7:30 It’s like, oh my gosh, so and so just came out with something new and we all have to have it. But more often than not, we come out with something new and it’s like, no, there’s nobody there. Nobody cares. Where is everybody? I thought we were having a party and so yeah, most of our conversations when we’re in groups of sort of like, is there a way to sell first and build second? Is there a way to get in front of customers now and get their buy-in their thumbs-up? Yes, I would like that. I would buy it, better yet, I will buy it! I will commit to buying it, if it’s ready by this date, I will in the best case scenario, pre-pay for it. Right?! Why not start at the cash flow now even before the product’s ready?
Brandon: 8:11 In exchange for what? You don’t have anything to give them yet. Well, you could make sure that they get it first. I’ve been inspired by my uncle who’s an inventor in this respect. I go, well, how do you, you know, you’re inventing these things and how do you get them to market? He said, well, frequently what he will do is go into this new industry for which he believes he has a solution and talk to multiple companies and say, well, whoever of you commit first, you’re going to get the product with a six-month lead over your competitors. I won’t sell to them for six months. You have six months in the market with this great product that’s going to give you a huge advantage with your customers. And that’s been a very successful model.
Brandon: 8:49 And when he first described that to me it was revealing because I was like, what? You know, you have to have something in order to sell, like a retail environment. No, no, you don’t. You know, you can make commitments. I went to law school, right? You can write a contract for anything and so it’s coming up with a way that both parties feel like they’re getting the benefit of the bargain and going out to customers early and saying if we have this, what do you want it to look like? And then really get into the weeds. We’ve had this happen to us where customers say “Oh, we have to have to have to have to have to have this feature, it’s the most important thing of all time.” And sometimes it is and so thankfully we spent a lot of time listening to customers and built some of those things that have just been windfalls for them and for us, but other times they’ve been wrong. Which is to say they think that they want it, where they believe that they’ll use it, and it’s an honestly held belief. And we think they must, you know, we’re hearing this everywhere and then we build it and no one actually uses it.
Brandon: 9:40 It turns out that, as a result, we were wrong. It wasn’t that important. There are even some features where no one necessarily uses them and yet, they’re still important for us to have from a marketing standpoint because everyone thinks they need them. And so we say, “Yep, we’ve got that”. And it’s true. But we know when they actually onboard, it’s one of the things that they’re less likely to use compared to other features in the app that are used all the time. So yeah, I think it’s continuing to remind myself to wait before we go down this path of adding a new feature, or adding a new product, or doing some big integration, can we get some validation? Can we get people saying, gosh, yeah, I really want that? Why do you want it? How exactly do you want it to work?
Brandon: 10:20 Not just generally like, yeah, you should totally build that. I think that’s one of the risks and we’re in the software business. It’s a risk for us and probably a risk in other industries. One of the risks for us all is once you have a super-talented engineer like Ryan, and he’s built a great team around him, there’s a lot of people, customers, companies that simply want them to build software for them all the time. You guys can build software, you should totally build it. All of us that are building software know that that takes a lot of time, a lot of effort, and a lot of money to do. So you don’t want to necessarily release a feature that you will need to support until the end of time unless it is that important. So yeah, I know a wide-ranging answer to a relatively straightforward question. We’ve gotten into trouble a few times by building stuff that we thought was going to surprise our customers and those surprises almost never have turned out to be the boons that we thought they could be.
Mark: 11:06 When you look at some of the things that happened that were kind of unexpected, I think about the one that you guys talk about fairly frequently, is Salesforce removing you guys from the App Exchange and maybe something that you didn’t have any idea that was coming your way. I want to combine that, that unexpected thing that happens, with this question: what kinds of things do you do to increase your mental endurance to deal with those things that come out of left field that blindside you, and like you said, you know, really could potentially take down the company? Just thinking back on that experience, are there things that you would do?
Brandon: 11:42 Yeah, yeah. That was certainly what we would describe as a mentally taxing experience. So to give some background, we’d launched Cirrus Insight on the Salesforce App Exchange. It was a brilliant echo system for us, right? It accounted for the lion’s share of our highest, and best qualified, leads when we launched back in 2011 and through 2012 and 2013. So you know, we had built it up to a point where, you know, last year Cirrus Insight had more reviews than any other sales operations, sales enablement app of all time. We’re the third most reviewed app between DocuSign and EchoSign, which was acquired by Adobe and became Adobe Sign and then Cirrus Insight, so we had like 3,000 customer reviews, which in an Amazon world, as we all know, is so important. You get that social proof and all this great SEO because what I found on the marketing side of the house is I can try to come up with the best slogans, the best way to explain our value proposition, but the customer always, meaning 100 percent of the time, says it better than I can or than our marketing team can or than a marketing consultant can.
Brandon: 12:44 The customer is just straight to the point. This is what I do with it and this is why it helps me. And so having those reviews, and we still have them posted on our website, was so valuable to us. We can point everyone to that. That said, that’s not our marketplace, we don’t control it. Just like Apple controls iTunes and Google controls the Playstore, Salesforce controls the App Exchange. So when it got to a point where they did an acquisition years ago and introduced an app that tacitly competed with Cirrus Insight in the marketplace, then we, like Marketo and HubSpot and Eloqua before us, once Salesforce had their marketing cloud, you know those applications are no longer on the App Exchange.
Brandon: 13:25 Similarly, we’re no longer on the App Exchange. And so that was something where obviously we had largely built the company through that channel for several years. Thankfully, however, we had invested quite a bit of time and energy and we had the benefit of building up a customer base over five, six years to the point that most of our traffic at that point was coming directly to us. It was coming straight to us through word of mouth, straight to the website, straight from SEO, straight to our content, our big opt-in mailing list. And so when we were actually removed, it had less of an impact than some would think. That said, and like I described before, my role is go to market. So when I think of it in terms of like retail goods, cool, the main artery was just closed, you know, we can’t take our goods on the river anymore.
Brandon: 14:12 It was dammed up. That’s over. Have we done enough work in the background to go over land? Can we take it another way? Can we airdrop it in? Can we get it to our customers through some other route so that we don’t have to go just through the marketplace? And thankfully we had done some of that work and then obviously when it happened we were able to double-down on a lot of those efforts and make sure we were driving traffic through those other channels. But certainly, to your point, I mean, yeah, that was a mentally taxing exercise to try to turn the ship a little bit and move away from one go-to-market channel and try to exploit another when you’re just kind of used to doing it. So you know, for all of us, the markets are going to change. No matter if you’re in the market for six months or six years, something’s going to change about it. And so it’s pursuing the ones where you’re having the most success while also spending some time and energy thinking about what’s next because that channel may close.
Mark: 15:05 Such a good point because we’ve all heard the stories where Facebook has changed an algorithm, or Google has rejected an ad for a particular reason, or you no longer have your avenue, your one avenue that you were dependent on. The thing that I hear you saying that I think is so, so important is that because of your engagement with your customers and because of building a relationship with people, you wound
Mark: 15:35 up really being less dependent on the App Exchange for your sales because you had word-of-mouth, you had the customer testimonials, which as you alluded to, are so critical. They are so important for you to be able to demonstrate social proof that your product is functioning in the market like it’s supposed to. And so you relieved your dependency on the single place of selling your product on the App Exchange over time and maybe it happens invariably, just as you gain momentum and you produce a good product and people are talking about it and you get to move forward. In terms of preparing yourself mentally for that, maybe there isn’t anything you can do. Is it one of those things like with weight lifting where you just have to push the weight and until you push the greater weight you really don’t grow? And so you just kinda have to walk through that. There really isn’t anything that you’re going to be able to do to position yourself to prepare for it. You just have to respond?
Brandon: 16:30 Yeah. Largely I think that’s right. Probably the best thing to do, we were able to simply reflect on some of the other obstacles and hurdles that we had already overcome and just say, well, this is another one. It looks like a big one. Thankfully, we have a track record – we’ve been able to get over a few. Why should this one necessarily be any different? It’s a different scenario, so it could be different, but it doesn’t have to be. We can get over this hurdle just like we have the previous ones, so I think in a lot of ways it’s building up mental endurance simply by proving to yourself, in an iterative process that you can do it over and over again to the point that like, I’m back. I haven’t been riding my bike for years, but I’m back in training now to do a big fundraiser for Alzheimer’s research in October.
Brandon: 17:14 And so as I get back fit again, and you mentioned this earlier, it’s like sometimes you know, you don’t necessarily want to run marathons every day. You don’t want to go do the long ride every day to get ready. You’re going to, as we say in boxing, “punch yourself out.” You’re going to get exhausted. And so I was out on a ride a couple of weeks ago and I thought, shoot, I thought I was farther along in my training, but now I feel really tired. I don’t have the snap. I’m not pushing the gears as fast as I thought I could, but then I was remembering years ago, I was like, yeah, this always happens. Right? When you’re in the middle of training, you always get to that point where you’re like, oh, I guess I’m not as far along and you’re like, you actually are. You’ve just kind of exhausted yourself temporarily.
Brandon: 17:53 So, it might be time to take a day off and then get back into it and thankfully, the training is there. Training is in the legs, but you do have to give yourself little breaks from time to time. To your other point, the relationships with the people have been the most important because it’s one of those things. There was a lot of emotional energy and kind of relationship friction oriented around, you know, not being listed on the marketplace anymore. We always tried to prioritize the relationship with the people. I mean obviously, our relationship with Salesforce is important to us. We’ve been a partner of Salesforce for seven-plus years, so we wanted to make sure at a personal level that we maintain those relationships and that we continued to do business together to serve our mutual customers. Thankfully, yeah, even though we’re not technically listed on the marketplace, we still get a lot of our best referrals from Salesforce because we can do unique things with our application that no other application can, and that their customers need.
Brandon: 18:44 And so we wanted to be still on the speed dial when their customers needed that for them to say, “Oh yeah, they’re not necessarily on the App Exchange anymore, but we can absolutely call Brandon and Ryan and, you know, get them to fly out and sit with this customer and solve their problem.” And so we still do that and that’s been really important. Kind of separate, and this has been really difficult I think for me and probably for most of us, was to separate the, hey, this was a business decision, these things happen. Channels and go to markets change, right? Google’s gonna decline your ad. Apple’s going to remove your app from the App Store just because their terms of service or they made a business decision. On a personal level, we can maintain those really important relationships with the people that are running the show at these huge, fast growing successful companies so that we position ourselves as small companies in the best place possible so that we don’t get steamrolled, which is always a threat.
Mark: 19:36 Brandon, is it critical that optimism be present in order for you to have success in this space?
Brandon: 19:43 It’s a great question. I’ve always considered myself to be overall optimistic. It’s interesting if I ask other people, right, if you’re in a panel and other people are reflecting back at you, I sort of shared on a panel recently like, well, you know, historically and as a kid I was pretty serious. Everyone on the panel was like, Oh yeah, you’re really serious. And I was like, really? I thought I was always really outgoing and friendly with all of you. Like how did you know I was serious? But somehow that had come through that. But yeah, overall I consider myself an optimist. I think that things generally speaking are on the upswing. Right. But I also get really serious and I can go in the tank sometimes, which is helpful to have a co-founder that can say we’re all right, you know, surround yourself with positive family and friends that are lifting you up and giving you energy and not draining it away.
Brandon: 20:30 I think that’s super important. Is it a requirement? I don’t know, because it’s just so hard to tell on the outside. I mean unless you really get to know someone super closely like, like a family member, a best friend. Like is that person truly optimistic? Because you get such a range of personalities in any chosen career and entrepreneurship is no different where you’ve got entrepreneurs that are just like, “wow, this person’s magical to be around. Like they just imbue everybody with this energy and they’re natural leaders” where you just want to whatever you’re working on, I want to work with you on it because it’s so exciting and they just have a way to frame things and tell stories that are inspiring to everybody. But then you also get some entrepreneurs that are really not fun to be around that are like, “wow, that that person is, is not particularly nice.”
Brandon: 21:18 They run a wildly successful business but they always seem to be in a bad mood. They’re succeeding, but they don’t seem like they’re enjoying it. Are those people optimistic? Maybe they are. Maybe they’re like, hey, it’s always going to get better, but I’m just not predisposed to be happy about it, but it’s hard to tell on the outside. So yeah. That’s just to say I don’t know, but I think it’s an interesting question, right? If there was a way to tease out through research, through survey questions or analysis of people’s actions and decisions, whether they’re in fact optimists or not, I would tend to think if I were pressed, that the majority probably are because you have to get over that hump to start in the first place, which in most cases is kind of irrational, right? It was like what made you think you could start something and have it possibly have some semblance of success in the market and that’s kind of a big leap, but it requires a little bit of boosting up your own ego to even want to get in the game. So probably most of us have a, you know, maybe an overabundance of optimism.
Mark: 22:17 Maybe your point is that you just need to enjoy the journey regardless of whether you’re optimistic or pessimistic about the potential outcome. I think if you’re enjoying the journey and generally happy with your position at the moment and knowing that it can change is probably a big key. And I want to shift to a final question because I so appreciate all of the time that you’ve given us today Brandon. As you look at your experience, are there principles, or maybe a leadership principle that you would consider to be most significant and as you led and continue to lead Cirrus Insight with Ryan, is there something that kind of floats to the top that you would say, “There’s one thing I want people to walk away from this today knowing or remembering it would be this:” Is there something like that for you?
Brandon: 23:09 So I mentioned earlier, I’m a big reader. I love reading books. It helps me get out of the day-to-day thinking around the business and frequently I feel like I get to answers or am able to overcome an obstacle based on reading something that’s totally random and that helps me get there. A book that I read not too long ago is by an author named Gregory Boyle, a Jesuit priest in Los Angeles, that runs essentially a huge startup that’s a big, gang intervention program called Homeboy Industries. So it provides jobs and a big framework for helping people get out of gangs and help improve their lives. He wrote a book several years ago called Tattoos on the Heart and the crux is he really focuses, if you boil it down to that one word, that one characteristic or trait, he calls a kinship. I love that word, and he was a personal friend of Cesar Chavez who did a lot of work on behalf of laborers in California.
Brandon: 24:02 And uh, he tells a story of a reporter going to Cesar Chavez and saying, “You know, these laborers in the fields, they, they really love you, you know, like, like you’re their leader, but they’re very passionate like they love you.” And his response was, “Well, the feeling’s mutual, right? That’s why I’m here. That’s why I’m doing it. I love them too!” So I think, yeah, cultivating a sense of kinship, whether it’s among our own colleagues internally, whether it’s with our customers, our vendors, our partners with the community at large. Those are the most important. And I think powerful and poignant relationships is when you feel like other people really get you and you get them and there is a sense that we’re in it together. What are we in together? Sometimes we just don’t know. I’ve got a little plaque that my mom gave me up on the wall that says “it’s not where you are in life, it’s who you have beside you” and that’s a nice sort of maybe similar idea to kinship because who knows what’s going to happen next.
Brandon: 25:02 That if you’ve surrounded yourself with other good people, then you I think have a much higher likelihood of enjoying that journey. I mean, I think from a philosophical standpoint, I kind of have enjoyed, and I’m not going to cite it right because I’m not sure. I don’t recall exactly who has been delivering these speeches, but they’ve said “failure does not need to be something that you obsess about too much because everything fails. It just depends on the time scale that you’re looking at it.” So things can succeed wildly for one year, five years, 10 years, but eventually, it’s one of those like the t-shirt. Gravity always wins. Eventually, the thing is going to fail. And so in some ways, it’s like, “oh, that’s terrible. Everything’s going to fail. That’s awful. It’s very fatalistic.” But on the other hand, it’s kind of relaxing. It’s like, okay, good. Then we don’t have to be so obsessed with like whether identifying whether or not something has succeeded. Right? Did it reach its full potential? Did it grow faster than any other company ever? Right? Was it the best and most bug-free software of all time? And instead, let’s just do the best we can for as long as we can. Enjoy the kinship along the way and hopefully keep the success running. And if it does fail, then it was on its timescale. Go to the next thing and hopefully build it again.
Mark: 26:12 It’s been a pleasure having you on the show today, Brandon. How can people learn more about you and what you’re up to and connect with you?
Brandon: 26:21 Well, thanks so much for having me, Mark! I’m easy to find. We’re a company that largely lives in the Inbox, so firstname.lastname@example.org is my email. BrandonBruce on LinkedIn. I’m also on LinkedIn quite a bit. For any of the listeners that may be in the Knoxville area or visiting Knoxville, Tennessee anytime, definitely look us up and join us for a Friday company lunch or we’ll show you around Knoxville. It’s a great community and a great place to build a company. So give us a shout if you’re in town.
Mark: 26:46 Wow, what a kind gesture. Brandon, thank you for taking the time to join us today and sharing your thoughts with us and I look forward to talking with you again soon!
I hope you were taking notes! Here are my key takeaways from Part Two of my interview with Brandon Bruce:
- don’t wait for the perfect product to launch
- be curious, be a student because YOU have to be the expert in your business
- get customer buy-in (and preferably their cash) prior to releasing a product or feature
- sell first, build second – create cashflow
- there is tremendous value in testimonials – the customer always says it better than we can
- avoid selling all of your product through someone else’s channel – focus on what’s working, but apply effort and thought on alternatives
- remind yourself of obstacles and hurdles overcome – it’s an iterative process for building mental endurance
- don’t burn bridges, remind yourself that often it’s a business decision, so keep relationships the top priority
- cultivate a sense of kinship with your colleagues, customers, vendors, partners, and with the community at large
- it’s not where you are in life, it’s who you have beside you
- everything is going to fail, don’t obsess over whether it reached its full potential – just do the best you can for as long as you can
Resources Mentioned In This Episode:
Gregory Boyle’s Homeboy Industries website
Brandon’s email address: email@example.com
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