“Failure is good,” and 99 other lessons from top business leaders

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When you’re focused on growing, it’s easy to get swept up in forward momentum. You’ve got your eyes on the next block to tackle, the next mountain to summit, the next pothole to avoid.

It’s not often that you take the time to pause and reflect how far you’ve come.

Today, my team is taking a little pause. The Growth Show has hit a big milestone: Episode 100.

Instead of catapulting ahead to the next 100 episodes, we want to take some time to reflect on the past year and half, and share what we’ve learned.

On the podcast, we brought back one of our past guests, Guy Kawasaki, to talk about the social media trends that have emerged since he last came on the show. You can listen to the episode on iTunes, Overcast, Soundcloud, or wherever you get your podcasts.

We’ve also compiled 100 of the best lessons our guests have shared about entrepreneurship, sales and marketing, leadership, hiring, and career growth. Check them out below, and be sure to highlight and comment on your favorites.


1) Mike Brown, Founder of Death Wish Coffee

“When I quit my job one day, one of the other employees said ‘Mike, you’ll be back. They always come back.’ I used that as motivation for starting my own business, thinking ‘I can’t fail because if I go back I’m going to have to look that guy in the eye and tell him he was right.’”

2) Beth Doane, Founder of Raintees

“As an entrepreneur, failure is an everyday activity. It’s how you manage it that determines your success.”
“You have to be able to ebb and flow as a business grows. You can make a mistake, you just have to say, ‘What did I learn from this mistake,’ and just keep moving ahead.”
“When you’re always clear on where your company is going, you can always be clear on the plan to get there. Too often, companies take what they have and make it bigger. They take what’s effectively a big hairball and just add to it, instead of saying, ‘We’re going off in this direction, how do we get there?’”
“I think that simple wins. In a world where everything is available to everyone all the time, I think to do one thing well really cuts through the noise and puts you in a place where you can be meaningful.”
“Because of all these different variables, you get hit with millions of decision points every single day. Until you generalize your decision-making process into principles and beliefs, you’re going to burn out every morning answering, ‘no we can’t build this,’ ‘yes we can build that,’ ‘no we can’t do this,’ ‘no we can’t do this like that.’”

7) Gihan Amarasiriwardena, CEO & Co-Founder of Ministry of Supply

“Crowdfunding is not just a means for raising capital, but it’s also for jumpstarting an amazing customer base.”
“Our friends would come to us and say what happened in the world today, and over time we started to see a pattern in the questions our friends were asking. We realized there was clearly a disconnect between how our friends were consuming media and information and how all these outlets were trying to reach them.”
“If you’re going to start a company, you have to do it for the right reasons.”

10) Kevin Mehra, President & Founder of 90+ Cellars Founders

“Don’t build a company for an exit because if you are, it means you’re not passionate about what you’re doing.”
“The most difficult thing about growing a startup is you have to learn new stuff everyday. You have to become the expert, you have to figure out how to do it.”
“When I started Blue Bottle Coffee, I had two credit cards and $20,000 or $30,000 thousand dollars to my name. I was a clarinetist, so that seemed like so much money. Of course I could start a business on that.
So that’s what I did. I didn’t know that that wasn’t enough money. I didn’t know that you should have this thing called a business plan. I didn’t know that there’s all these hurdles that, since I didn’t realize that they were there, I didn’t have to go over them. It’s a little bit ‘ignorance is bliss’ — but it was really good training. I learned you’ve got to make money before you can spend it.”
K: “It makes me cringe sometimes when I hear stories of people who started with $2 mil in the bank and 10 months later they have no money and aren’t able to pay their 30 employees.”
J: “We’re always going: Do you know what I could do with $100,000?“
“I was incredibly naïve about many things. Let’s just start with raising money, finding an investment for our business. I now know that the Silicon Valley VC startup world was probably not where I should’ve started. There are other kinds of investors. There are other people who invest for various different reasons that might’ve been a little bit more receptive to the message. You don’t need to come out of the gate proving at a 10X or 100X multiple.”
“There’s the difference between smart money and dumb money. Max Levchin is smart money. Even if you were to take money from Max — and let’s say he may not be willing to invest at the crazy valuation that you ideally want — having him as an investor in your company will pay dividends in the future. That valuation difference doesn’t matter. The difference between smart money and dumb money is that smart money will help you through whatever crazy situation you have.”

16) Anna Bond, Co-Owners & Creative Director of Rifle Paper Co.

“We started out approaching the product line somewhat naively in the sense that we would just figure it out as we go — and there was a lot to figure out. It hit home the day we launched our site and being bombarded. Everything sort of became a reality and we realized how little we knew and how much we needed to learn.”
“I always try to not think that my babies are too beautiful. And you can fall in love with a problem, but don’t fall in love with a business because you won’t change it.”
“As a company when you’re starting out do something that matters, have conviction about what your business stands for, make it mean something more than making $120 million or delivery the next quarterly profits.”

19) John Kimmich, Owner of Alchemist Brewery (Heady Topper)

“That’s the basis of our entire business, focusing on quality. I’m certainly obsessive compulsive when it comes to our beer and that’s important. I feel that that’s a big part of what’s going on. There’s a lot of breweries out there that say they have attention to detail but I don’t believe it.”
“It seems a little counter intuitive, like it’d be better to start with a smaller idea that you can see a path to a million dollars, but it’s actually better to go after ambitious ideas. If you choose an ambitious idea, it’s just as hard as a smaller idea, but you get a lot of benefits for doing the ambitious idea. Press, employees, and investors are all attracted to ambitious ideas. And, if you mess up on the ambitious idea, you can often find success doing something else in that market. If you pick something niche, you’re kind of dead on arrival if it doesn’t work.”
“Don’t do it for the money. It’s a hard lesson to learn because the startup fantasy is that this is an amazing way to get rich and become a billionaire. You’re just bad at math if you think that’s the case because the odds of success are a little better than buying a lottery ticket. However, it doesn’t mean it’s not a fulfilling to do, I just think people need to do it for the right reasons. I have to admit, I did my first two companies for the wrong reasons, and I learned the hard way that I think it’s a mistake.”
“A lot of what the various competitors are doing is really shaping the category. So of course we stay true to our vision, our mission, and our goals, but we also have to pay attention to what’s going on in the market place.”
“We’ve always grown by just anchoring to what problems can we solve for people who want to cook.”
“When you’re starting out, especially early on, everything looks like the problem [you’re trying to solve]. But if the problem is that obvious, people would have solved it by then.”
“Taking something in an industry that has been very painful — waiting in line at the post office, trying to package something — and just completely making it friction free, I think is how we’ve gotten a lot of buzz.”
“It’s easy to rush into building a company. There’s so much of a narrative, especially around startups nowadays, on the lean startup, testing, and MVPs. Ideas are cheap, and execution is what really matters. I’m not saying that those are wrong. But I do think there’s this kind of current failure in the system for people to really go for big, crazy things.”
“Being too early and trying to be in the future prematurely is actually worse, in many ways, than being too late.”

Marketing & Sales

“When you call it a marketing team, no one knows for sure what you’re supposed to do. But when you call it a growth team, everyone knows exactly what the goal is and what you need to do everyday.”
“Marketing doesn’t define what a brand is. A brand is made up of every single interaction someone has with your company.”
“I think I’ve managed to, in the midst of seeing some terrible, terrible things, stay really focused on the hope. It’s because we are a brand of opportunity and hope, not a brand of guilt and shame. We don’t want your money if you’re giving because you feel guilty or shameful. We want your money if you believe that your generosity can actually make an impact on people.”
“Making decisions takes time and energy. If you can make a decision once, then the question isn’t ‘should I do it?’ it’s ‘what will I do?’ So if you make the decision once to be a vegan, then you don’t need have a discussion with yourself every single night about whether to have a hamburger or not. And if you make a decision to blog every day, then the only discussion you have to have with yourself is ‘What blog am I going to do?’ not, ‘Should I do a blog?’”

32) Tomasz Tunguz, VC at Redpoint Ventures

“Content marketing is a little bit like a bank account where you get the benefits of compounding returns.”
“I don’t want positive, supportive, wonderful, reinforcing engagement on social media. I want any kind of engagement.”
“Nobody wants to be the subject of negativity and vicious attacks at the time, but I think often when there is controversy around something, that just catapults people into the discussion. I think if there’s controversy about things, good or bad, it puts you on the map.”
“The number one mistake people make is assuming the customer is ready to buy the first time they come into contact with your business.”
“Sometimes we have to stop asking consumers what they want and instead focus on the way the they’re actually behaving.”
“We never paid to do user acquisition, we have never done advertising. We’ve been lucky enough that building a good product really generated word of mouth for us and made it easy for the product to continue to grow.”
“I’m all about quantity. I understand you want quality, you want to be kumbaya, you want to be transparent, you want all that great stuff. I’m not one of those types of people. I think that the more people who follow you, the more powerful the platform.”
“The reality is, if you put constraints on yourself that allow you to operate principled, all of the same growth practices with can absolutely still apply.”

40) Andy Goldberg, Chief Creative Officer of GE

“I think the first thing we look at is who are the right partners to build this with. Having great partners is what makes us successful and what makes any brand successful if you have partners you can trust.”
“Audio podcasts are always third on the list of marketing you should do. Text blog posts are first because they’re the easiest to pass along. Then it’s video, because up until now, it’s had a better chance of going viral. Podcasting is pretty deep down there, but the tradeoff is when you do attract podcast listeners, you’ll have ’em for life.”
“I do believe the world is becoming a potentially more addictive place, and it behooves us to understand these tactics so we can put technology in its place.”

43) Jason Bosinoff, Engineering Manager at Airbnb

“It’s better to have 100 people love you than 1,000 people like you.”

Leadership & Management

44) Jeff Rosenblum, Author of ‘The Naked Brand’

“Great leaders are able to find small pieces of friction within an organization, and remove them.”

45) Daniel Koh, Chief of Staff for the City of Boston

“People want to hear from their leader. They just do. Leaders especially sometimes undervalue that, whether it be humility or the pace of the day that makes them forget about context of how much influence they have as leaders. Make sure that whoever the leader is in your organization understands the influence that they really have.”
“Leadership boils down to a series of one on one conversations. You can aggregate those. You can follow those up with larger communication to bigger audiences, but it really comes down to talking with someone, looking them in the eye, understanding where the leverage points are in the organization, helping them, taking an idea from your own mind to theirs, and using that as really the way that you move a group in the direction you need to move it.”
“I think our transparency through Startup has been incredibly valuable. Employees are attracted to having a place where they know the leaders of the company, they can relate to them, and they know that we’re honest. To use a word that has a lot of different meanings, it’s authentic. What we’re really trying to build is trust with our audience, and being as transparent as you can is the best way of doing that.”

48) Scott Meyer, CEO of Ghostery

“The start to transparency has to come from understanding what your team needs. Because just barking up your financials and doing lots of long Powerpoints, and in fact just doing stand ups too frequently, creates just too much noise.”
“I think that’s one of the things that I’ve learned about being the CEO of something is that there are scenarios where you don’t want to be transparent about the way you’re feeling or about what you’re thinking. You don’t want to share every thought that you have. That’s not your job. Your job is to be as transparent as you can be in a way that helps your employees and the company.”
“If you really want transformational results, you need a new form of leadership that embraces the head and the heart, the operator and the person, that’s open to doubt, and makes it safe in order to talk about. Because that’s where you can really start to drive results and accountability. If people can feel safe, innovation and new ideas can really flow.”
“One way to think about feedback is the same way that I think about writing novels. The most important advice to writers is show, don’t tell. In other words, you wouldn’t say ‘She’s really smart.’ You’d say, “She could do The New York Times crossword puzzle in two minutes.” You want to show exactly what you mean.”
“At Harry’s, we talk about the fact that feedback is a gift. It’s never about who you are as a person or your intentions. We all know that we’re good people, and we have the best intentions at the right point in time. It’s just about correcting behaviors that people have that don’t lead to the best outcomes all the time.”

53) Julie Herendeen, Former VP of Marketing of Dropbox

“Jim Barksdale at Netscape was such a great leader. He would tell us, ‘If you see a snake, kill it.’ It really meant that if there’s an issue that keeps coming up, you need to wrestle it to the ground. You need to identify it, you need to figure out what you’re going to do about it. He also had a related saying: ‘Don’t play with dead snakes.’”
“There’s always a organizational structure, whether or not you define it. We hadn’t defined our company’s structure, therefore the structure was inefficient. It meant that some people, like myself, were involved in every single meeting or decision. That really started to break at 20ish people. But I realized, if we have a structure but we’re really clear about what it means to report to somebody, and we’re really clear about what it means to be a good mentor and leader, that your company is in a really different spot.
Once we started to do that, what happened is I started being in a hell of a lot less meetings, and I started to not know what was going on because everyone was doing great stuff.”
“Have conviction. I think as a company grows, and as it becomes more clear that you’re doing something really different, the more often you can repeat what you think the world’s going to look like and how you fit into that five to ten years down the road, the easier it is to get alignment from your partners and customers.”
“One element of leadership that gets overlooked sometimes is the courage to be vulnerable first. Sometimes parents will ask me, ‘Frank, how can I get my son or daughter to open up with me the way you do at PostSecret live events, where audience members will come to a microphone and tell their secrets, not anonymously, but very publicly for the first time?’ My answer is always the same, ‘If you wanna hear somebody else’s secret you have to be strong enough to tell one of yours first.’”
“I think everybody has the ability to have a prophetic imagination to picture a future where everyone thrives and it’s the leader’s job to stay connected to that. So my role is to move between today and tomorrow, compare today and tomorrow and the future.”
“You can have the greatest strategy in the world, but if you don’t have a great culture to execute that strategy, you will lose. Culture eats strategy for breakfast every single day.”

59) Will Dean, CEO & Founder of Tough Mudder

“Don’t try to be the Marriott Hotel for your culture. You don’t have to set up an enjoyable stay for everyone — and you should be OK with that.”
“Show up to work as a human being. For some reason, many people think it’s ‘unprofessional’ to bring their whole self to work. But I think you’ve got to show up as a lot more than ‘professional’ — you have to bring your whole self to work if you want to be a great teammate.”
“When we hire, we look for past experiences that show people are deeply empathetic. We try to screen out entitlement and arrogance because we find that’s in marked contrast to being overwhelmingly friendly, apologetic, and empathetic.”
“We are comfortable with who we are, which allows us to be who we are, we attracts more people to our company who like who are and also repels the people that don’t.”
“An empty seat is better than hiring the wrong person.”
“Now the big thing is having a team of really creative people who have, what we call, ‘humble confidence’ where they believe they can do big things but are humble about they do it. It allows them to experiment and try things without being afraid of failure.”

65) Todd Rowe, Managing Director, SMB Global Sales at Google

“Great ideas for a company come not from the executives. They come from the individual employees. Giving them a vehicle to do this, like the 20% project, is a great way to drive innovation.”
“Healthy teams are teams that look at change as an incredible opportunity instead worrying that things aren’t the going to be the way they used to be.”
“I think that there’s this proliferation of group chat going on right now, and it’s actually ultimately not a very healthy thing. It forces every decision to be knee-jerk and quick, and people feel like they have to get their word in. If they’re not there at the very moment the discussion’s happening, they’re left out of it. Sometimes you just need to slow down a little bit, gain some traction, write something up long form, and give people time to think about it.”
“When you get to the heart of what culture is, my definition is the attitudes, the feelings, the values and behaviors that characterize and inform a group and its members, but if you take a step back from that definition, it’s who you really are so the culture of any organization comes from the people because the people make up your brand.”

69) James DiSabatino, Founder of Roxy’s Grilled Cheese

“In the restaurant business, I’ve never understood the concept of growing quickly. I feel like growing quickly comes at a huge cost to a company culture. I think of baking — you’re not going to find a way to bake muffins faster. It’s something that just takes time, and every little aspect of it is important. If you’re really looking to put something out that reflects you, speeding it up doesn’t actually get you the results you want.”
“Not everybody you hire is going to be the best person that you hire for your team. If that’s the bar, you won’t hire a lot of people. When we think about bringing someone in, the next engineer we hire should be above the average of the current existing team. The next sales person we hire should be, based on all the data that we have, above the average of the sales team. If you keep that bar at or above the average, then your team just gets better with time.”
“A lot of people think that the executives are sort of the tip of the spear of the organization, and for us it’s actually the inverse. It’s the employees on the front lines of building stuff, working with customers, selling to customers, that are the efficient frontier of the company and I’m in the back, trying to digest all of the signals they’re sending.”
“Sometimes, the hard stuff, the impossible stuff, the it-can’t-be-done stuff is the stuff that spurs us on and makes us great. Sometimes, we spend way too much time worrying about morale in those situations instead of worrying about getting things done.”
“I just think that, typically, when people really want to get stuff done, they need to be left alone to do that. Offices are not places you go to be left alone.”
“We’ve got flex time [at Patagonia]. If the surf’s good and you can get away without compromising your fellow workers and leaving them hanging, well, leave and go surfing. Because you can’t schedule good surf.”
“When you are prepared, you are more likely to make lucky guesses. You’re more likely to see opportunities and anomalies around you, and to be able to join together dots that haven’t been joined together before.”

76) Marc Maron

“If you’re lucky and you have a certain amount of talent and you keep your shit together, you’re afforded opportunities and sometimes things turn out well.”
“Be comfortable with adversity. If you’re the weird one, figure out how to make it work for you.”
“Experience is what you get when you don’t get what you want, and I have a lot of experience at this point.”
“Always invest in yourself, in your network, and in your relationships as soon as possible. Don’t think that you’re going to build a business today, think long-term.”

80) Kai Kight, Keynote Artist & Violinist

“Don’t wait for permission, especially when it doesn’t have a lane.”
“Being humble keeps you hungry. If you start to feel too confident and think everyone loves you, you start to approach things differently.”
“When you do very few things, you can focus on the things you are doing, and do them very well.”

83) Payal Kadakia, CEO & Co-Founder of Classpass

“I went on this journey last year to not change who I was at my core (which can be tempting when you’re building a high-growth company). I realized that I want to stay who I am. That’s what made me Payal, and that’s what made this company what it is today.”
“25% of all graduate school graduates opt out of the workforce at one point in time. We can not as a society afford to lose 25% of that brainpower, we have to bring this group back into the workforce.”
“Giving people the opportunity to relax into their own eloquence is the best thing we can give young people. It helps them generate the confidence they’re going to need in order to tackle the big problems in this world.”
“There are a couple other incidents in my life as an outdoor adventurer where I’ve actually gone over and kind of looked into the dark side where you didn’t think you were going to come back, and I have. So I’ve been there before. And I’ve discovered through those experiences that the ultimate value of them is what we should all be doing every day of our lives, and that is, as frequently as you can, pausing. Just making a little pause to look around you, to acknowledge the good people around you, to acknowledge the beauty around you, even as simple as standing outside and feeling the sun warm your skin.
Learning how to take the most value from the simplest things in our life, it really is the secret sauce. And it’s too bad that sometimes we have to almost die to remember to do those simplest things in our life, and to just understand deeply the value of those small things — because there’s nothing small about them in that context.”

87) Neil Pasricha, Author of ‘The Happiness Equation’

“No advice is true in every situation. When we’re looking for advice, usually, we’re looking for an alibi. And the point is: If something resonates with you, if I happen to write something that you agreed or disagreed with, great. But it’s actually a reflection of you, not of me. You already had that feeling.”
“Everything you do in your life falls in three buckets: bad work, good work, or great work.”
“It does not matter how creative people are. What matters is how creative the process is. There’s no such thing as a creative or uncreative person, there is just a process that is designed to make innovation more productive. If you buy into that process and you commit to it, you will get something good that comes out of the other end.”
“I don’t really know if I believe in this idea of work-life balance, this idea of turning off. I think at this point, I’d rather just be one person and accept that work and life are pretty intertwined.”

91) Neil Pasricha, Author of ‘The Happiness Equation’

“Listening to your gut is the dream, but it’s not always easy.”

92) Michael McNally, Senior Director, Brand Relations at LEGO

“What motivates me at work is what does reward and drive me in my personal life. I think there is a huge difference between getting up every morning to make a difference in the world than there is to get up to make money … No one at LEGO goes to work to make money.”
“Failing is the one thing I’m really good at. I’ve failed a lot in my life. I’ve done a lot of different things, tried a lot of different things, and seen some pretty big dreams fall away. Through all that, I’ve kind of got this idea that failure is awesome. Failure is good. You learn from it and you pick yourself up and you dust yourself off and you keep on moving.”

94) Bill Walton, NBA Legend

“Have a dream, choose a teacher a leader a coach, join a team, immerse yourself in the positive culture that’s already there. Develop the individual foundation, assuming and understanding that the team is the strength of the individual and you’ve got to have it yourself before you can make the positive contribution, and then the willingness to sacrifice and discipline.”
“I’m always trying to find something about myself or my career where I’m at the bottom of the learning curve so I can feel like I can have that sense of being a beginner. It makes me feel like I’m 12 years old — there’s this sense of being really clueless and then progressing. It’s very refreshing to continue to feel that way.”

96) Victoria Ransom, Co-Founder & CEO of Wildfire

“I truly believe I learned more through travel than I ever learned in school or any kind of any education. I’m just a big believer in the power of meeting people from different cultures and exposing yourself to different countries to help you get inspired, help you understand others’ lives better, help you understand yourself better.”

97) Frank Warren, Creator of PostSecret

“Looking back on the project now from where I sit today I think one of the reasons I was so driven is because I had secrets I was keeping from myself at the time. It was through PostSecret and creating the safe nonjudgmental place where people could share with me that I was able to uncover some of the secrets that I had buried long ago. In some ways maybe this whole project has just been a journey of therapy for myself.”
“I asked myself, ‘In ten years do I want to wake up and still be doing this?’ and the answer was no. And now I ask myself that all the time. If I’m starting a project, I think ‘In five years if I wake up on a winter morning and it’s raining and it’s cold like it is today, will I still want to be doing this?’”
“Be okay with that ambiguity because something good is going to come out the other end.”

100) Bill Walton, NBA Legend

“It’s the things you learn after you know it all that count.”

From all of us at The Growth Show (I’m looking at you, Kipp Bodnar, Meghan Keaney Anderson, Christine Ianni), thanks for celebrating with us.

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