Learn from every “no,” w/Walker & Company’s Tristan Walker

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I have been turned down a hundred and forty eight times. That's Catherine Minshew. Co-founder and CEO of The Muse, a career development website that she pitched to investors 148 times. Not that she was counting. There were literally days where I had a no-over breakfast, a no over at ten thirty AM coffee.

and no over lunch, you know, disinterest at 2 p.m. Um somebody who left a meeting early at four. And then I would go to drinks and feel like I was being laughed at the moon. And when we finally raised Our seed round, I went back and counted. It was both painful and gratifying at the same time, looking at all those names and thinking, I remember that no, I remember that no, I remember that no, and they stink. Everyone stings.

Today the Muse serves users in the millions. Katherine raised sixteen million dollars last year. And her tale is the origin story of most great startups. So if you're hearing a chorus of no's You should look for other signs that you're on to something.

I believe that the best ideas often appear laughable. At first glance. You gotta have incredible talent at every position. Huge push. There are fires burning when you're going out. Can you believe it? Such an idiot. And then you go back to this is totally gonna be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Like, well that's just how you do it. We haven't made just how you do it.

This is masters of scale. I'm Reed Hoffman, co founder of LinkedIn, partner at Greylock, and your host. I have the theory that the best business ideas often appear laughable at first glance. The lesson for entrepreneurs goes deeper than the pat advice you shouldn't take no for an answer.

you should expect to take no for an answer. If you're laughed out of the room. It might actually be a good sign. I'm gonna test this theory by talking to some of the smartest people I know.

many of them have spent time in the rejection line. Google. Facebook, LinkedIn, Airbnb. all sounded crazy before they scaled spectacularly. On this episode of Master Scale, I want to help you see what the transformation from a crazy idea

to a clearly good idea looks like. and what signs to watch for along the way. We'll talk to several CEOs. but we'll focus on one entrepreneur's journey. From beginning.

Now. It starts in a city. Far, far away. From Silicon Valley. So you're not one of those classic kind of Silicon Valley geek people.

That's Tristan Walker. The founder and CO of Walker and Company. Their flagship brand is Bevel, a razor for men with curly facial hair. He started as a kid in the projects. You know, I I like to say I had the whole rose that I grew from concrete story, right? Yeah, I grew up projects, welfare, all that jazz.

And I had one goal in life. And now to get as wealthy as possible, as quickly as possible. And I realized that there were three ways to do it. Uh, the first was to be an actor or an athlete. And that didn't work out for me too well at all. Uh the second way was to work on Wall Street. I had the good fortune to do that for about two years and hated it. So I said, damn, I've already exhausted two of the three. The last one is entrepreneurship.

Uh and the day I came to that realization, you know, I applied to the school Stanford for business school. Uh and fortunately let me in. And then I learned that Silicon Valley existed in the rest's history. So you came to Stanford not even knowing it was like it was the hardest. Tristan doesn't sound like your typical Silicon Valley geek. But I can't stress this enough. You don't have to wear a food stained hoodie to succeed here. Neither do you have to play World of Warcraft. Or write code until sunrise.

You only need to have a sense of curiosity. And Tristan. Was exceptionally curious. He wasn't just a student of business. He was a student of every technological shift.

taking place around him. I was in accounting class at Stanford. And uh I remember I believe MC Hammer was supposed to speak at Stanford and there was this commotion going on, people wondering if he was actually going to do it. And it was going around for like five minutes and I opened up Twitter and I just asked MC Hammer. I was like, Are you coming? Bear in mind this is two thousand and eight.

Back when Twitter had a relatively cozy community of five hundred thousand monthly users. Tristan was one of the more active members. As luck would have it, it was hammertime on Twitter. Thirty seconds later he replied back and I turned around to my fellow classmates and said, Yes, he's coming, see? And at that point I realized how important Twitter's part in like

the kind of innovations within communication were. And it was my first um understanding of bad ideas. being a good idea. Because everyone else around the table was like, Why are you on Twitter? What's the point of this thing?

I don't care about what you're eating for breakfast. And they just didn't get it. And that showed me that there was something there that I had to kind of dive into. So we're already seeing the seeds of Tristan's success. You don't have to be a geek. But you do need to geek out over the new ideas.

You want a level of enthusiasm that's slightly out of step with your peers. And Tristan was seriously geeking out over Twitter. He wasn't just an early user. He wanted to help build the company. So I emailed 20 different folks who I knew were either one or two degrees separated from the company. The last person I emailed was David Hornick, because he was a professor at Stanford and also partner at August Capital.

Uh he replied back, he said, Come to my office, let's talk. David asked me two questions. Tristan, are you willing to work for free for the summer? That's David Hornick, by the way. Right. And I said yeah. I'm happy to introduce you to Twitter, uh but I'm curious if you actually know what Twitter does. Yes, right. Um and at the time they weren't thinking about the business model and that sort of thing, and I was fascinated by what it could become.

Send me your resume and I'll send it to Ev. Probably two days after that, uh, Evan Williams sent me an email. Devin Williams is the founder and former CEO of Twitter. uh saying come in for an interview. Uh and a week after that, they gave me an internship at Twitter and I worked there for about six, seven months when there were twenty folks at the company. You may think Tristan is lucky to get an email from Ev Williams, but notice the size of Twitter's workforce at the time.

twenty employees total. Tristan spotted the company's potential not just ahead of his classmates. But ahead of the market. He has a knack for spotting ideas. right before blast off.

David Hornick noticed this too. Twitter was nothing when Tristan was excited about it. I mean Twitter was a place that you told your buddies. You were heading to the park. Twitter at the time was a service where you said I'm eating a delicious ice cream cone. It was entirely unclear what one did with Twitter. How one could make money at Twitter, how big Twitter would become Shortly after his Twitter internship ended, he started his next email campaign.

He bombarded the founders of a fledgling startup called Foursquare. And again, the CO Dennis Crowley Responded. I emailed them eight times. The eighth time.

Dennis sent me an email. I'll never forget this, verbatim. He said Tristan, you know what? I just may take you up on some of this. Are you ever in New York? Dense. Right, that's it.

I was in LA at the time and I was sitting on the couch uh with my wife. And uh I said, How should I reply to this guy? Ten minutes later I sent him an email. And I said, actually I was planning on being in New York tomorrow. I booked my flight that night, flew out the following morning, hung out with them for a week, and a month later I was running business development for the company. By now you may be thinking, Holy cow. CEOs are awfully responsive creatures.

But before you start dashing off messages to the employers and investors of your dreams, I should warn you. Few stories and like Tristan. I've had the experience where like I was walking out of Greylock and guys said I've been waiting here all day to meet you and I'm like, this isn't the way to meet me. I'm gonna continue walking in my car and I would try to get a reference to me. This will get me to never pay attention to you again. You go into my security services file of people to track.

That file exists. But Tristan's pursuit of Foursquare had a happier ending. That's because he targeted teeny early stage companies, startups with twenty people or less. The lesson here is not just his persistence. But as prescience.

Some people get lucky and board a rocket ship by chance. But two rocket ships? That's no coincidence. That's a sign. You can spot an undervalued idea ahead of your peers.

It's like the spidey sense that just keeps tingling. It's hard to stay in one job, even a wildly successful company. Once you've started sensing opportunities. All around you. When I started at the company.

We had zero merchants, zero brands, all that one platform. By the time I ended up leaving Foursquare even a couple years later. We had over a million merchants on the platform. By the time I left, we were 150 people I started when we were three. And quite frankly, I wanted to go out and build ambitious things myself. So Tristan left Foursquare in 2012. After building your business development team from the ground up. He then found the perfect place.

To plan his next move. Ben Horowitz, a founding partner at the iconic venture capital firm, Andreessen Horowitz, Invited Tristan. Just to hang around the office and think big. Ben said, come spend six to nine months with us to figure out what you want to do.

I spent all nine months there. And I like to say I spent the first seven months of my time there wasting their time. I wanted to build a bank, I wanted to fix rate and trucking, I wanted to fix obesity in the country and the world, right? Then Inspiration struck.

I just got frustrated by the shaving experience. A better shaving experience may not sound like the idea on the scale of freight trucking, obesity, or banking. Don't have to tackle dramatic problems. They have to tackle neglected problems.

And the more that Tristan looked into the history of shaving, the more he realized there was a hugely overlooked demographic. Men with coarse or curly facial hair Who had been living with the curse of razor burns and razor bumps for so long they no longer even recognized it was a problem. Let's just get a handle on this coarse or curly hair dilemma. Which I'll admit.

is outside my particular area of expertise Are you fed up with Razorburn? For decades, razor manufacturers have promised a better shaving experience. They identify the same problems. Are you sick of mixed cuts and unsightly razor bumps? And offer essentially the same solution. More blades in every cartridge. Not one, not two, but three blades. A lot more blades. That's right. Five blades to whisk away those stubborn whiskers. And this ever growing stack of blades did actually improve the shaving experience. For a lot of men. We tested our six blade razor on twelve hundred men. Two out of three reported a smoother, cleaner shaving experience.

But it mostly worked for white guys like me. White guys with straight hair. But the rest of the population, and especially African American men, were experiencing a multi-bladed assault. On their skin.

Their shaving experience got worse. And this went on for generations. Until a dive into history. Open Tristan's eyes.

That no one else could see. They reached out to an old retired um executive from a C P G company. He said, Tristan Look at photos of black man a hundred, hundred twenty years ago. None of them had razor bums with shaving irritation on their faces. I thought he was being facetious. So I said, I have time at Andreas and Hards, maybe just look it up. And I went to Flickr and I did enter these generic search terms like Harlem Renaissance, Black Men in the 1920s, that sort of thing. I went to twelve hundred photos.

and then find one with like a non-cleanly shaven face. And it had to do with you know the tools they used. In 1904, this whole industry was built. A gentleman named King Gillette. He had this amazing idea. He said for hundreds of years, Barbers have been used this thing called the straight razor to great efficacy. It cuts the hair level with the skin not beneath. But using a straight razor yourself at home is pretty hard to use if you're not trained. So he had this idea, he said, what if you can take a single blade, house it within a safe head, attach a handle to it, take it home with you and shave? And that started the mass market shaving industry as we know it.

Fast forward twenty years later, they lose the patent. And many would argue. Uh that the only reason we have two three four five six blade razors today is purely due to patent protection, but it actually has less efficacy and if you travel internationally, single blade is more popular than multi. His solution? He reengineered the single blade razor.

specifically for coarse or curly hair. He called it the bevel. and it became the flagship product. for Walker and Company. And the first step.

in his grand plan. He envisioned a health and beauty company on par with global brands. like Procter and Gamble. a company that devoted its attention To men and women of color.

It was blindingly obvious to him. That this company should exist. I mean, a lot of people say that they're trying to build the Brock and Gamble for people of color. Let me talk about this for a second, because it's really funny. Number one, I've never said that. And then two It was interesting. Like

I think folks talk about it as if it's a niche kind of thing, but people of color the majority of the world. So if we're the Procter Gamble for people of color, what the hell is Procter Gamble? But when you're pitching a room of mostly white Mostly male investors. It can be hard to convey the urgency. of this market oversight.

So how did the best and brightest VCs respond to Tristan's idea? I don't know, a sneeze. I don't think it's scalable. It's a terrible idea for me to kind of jump into the bevel thing because it was a consumer group who didn't want it, an industry that is dominated by the multi-blade use case with billions and billions and billions of dollars to attack you with patent protection, et cetera. Right. And to do it in like Silicon Valley, right? That's crazy. As is often the case.

There was one lone champion. And I go to Ben, he's like, that's the idea. And at that point I knew I had something. Quite frankly. This may sound like a strangely optimistic reaction. Why should a single endorsement from an investor outweigh a crowd of investors telling you, thanks, but no thanks?

Shouldn't you weigh all of the feedback equally? Short answer no. And here's why. The first truth of entrepreneurship and investing is that the very big ideas A contrarian

Because the Contrarian is part of the reason why a bunch of large companies and competitors haven't already done it. why a bunch of other entrepreneurs haven't already succeeded at it. And so that leaves the space. For the creation of something.

And to create something big, you have to have that initial space. For example, in the early stages of Google, it was Search is a terrible way of making money in advertising because advertising is time on site. And what does search do? It shuffles you off the site as fast as you can go. That's not a good business model. So like an Airbnb, it's like Oh, someone's gonna rent a couch or room from someone else? Who are the freaks on both sides of that transaction?

So all of these things have a similar quality. Very smart people will tell you there's no there there. So you have to gird yourself. For a string of rejections. Some entrepreneurs simply develop thick skin.

Others treat it like a normal part of their work day. You know, wake up, brush your teeth. Listen to people crush your dreams. It's a living. But there's another, more hopeful approach.

Our producer Dan Kedme Talk with a number of entrepreneurs. Who pitched seemingly laughable ideas. In all kinds of industries. Llock.

Founder and CEO of Global Citizen Year. Her not for profit sends students abroad for a year of international service. between high school and college. Back in two thousand eight. She was struggling to get funding.

And she turned to a leadership coach. For advice. We asked her to share that advice. The nose are actually a gift. You heard that right.

A gift. And he said between now and when we talk, two weeks from now, I I want you to go out into the world and gather as many nose. As you possibly can. It is your homework.

to be rejected over and over and over and over and come back and report on it. And it ended up being the most important thing I could have ever done and the most important advice I could have been given at that point. The most successful entrepreneurs listen closely to the nose. They mine their rejections for clues. Catherine Minshew, the founder of The Muse, got her share of rejections over the course of 148 No's she shared at the top of this episode. We asked her about the reasons that investors turned her down.

It's a bit too early for us, but keep in touch. Once you hit 100,000 monthly active users, give me a call. This is a fool's errand. It's expensive, it doesn't scale. That's not very tech. That's not a scalable platform. Aren't you worried that you're gonna lose all your users once they turn thirty and You know, have babies.

Or you know, I I get that women in New York and San Francisco love this product, but I think you're gonna really have a a hard time finding women who care about their careers once you go outside of, you know, the coast. And I just remember looking at these people and thinking, Do you know a lot of women? Catherine is right to ask this question. She knows more about women than most investors. And she also knows more about her business.

Entrepreneurs have to learn how to hold on to what they know through the arduous pitch process. And Carol Golden, the founder and CO of Hint Water, takes this a step further. when she was hard at work on a recipe for a flavored drink with no sugar or preservatives, a bigwig in the beverage industry, Offered her pointed advice. What I want you to notice is how Carol listened to his rejection.

She didn't just hear no. She saw the breadcrumbs leading to her own company success. His response was sweety Americans love sweet. that's really interesting that he just called me sweetie. You know, I'm a business person. I

been zoned out of the conversation and came back in, realized that somebody at a major beverage company basically was sharing with me you know, without him knowing it, that that was really what the belief was at this major soda company that Americans really love sweet. And so that was the fork that they were taking in the road and that I needed to put the gas on and grow this before they decided to come down my fork as well. Turns out that Care's Critic was wrong to the tune of ninety million dollars a year. That's how much revenue Hintwater takes in from Americans.

Who supposedly Have incurable sweet tooths. At this point You may be thinking about your own counterpoint to my theory. Sure, Karen Catherine ultimately secured financing and proved their critics wrong.

But what if you're pitching a truly terrible idea? How can you learn to hear that? When you build substantial wealth through your business, it's often tied up in a single equity position. The upside is real, but so is the risk, and knowing when to act isn't always obvious. Creative planning works with business owners to build a strategy around concentrated equity.

When to diversify, how to manage tax risk, and how to protect what you've spent years building. Creative planning where wealth works together. Learn more at creative planning dot com slash masters of scale. Hey listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may be missing half the show. Because every Friday we release a second rapid response exclusively in the rapid response feed. The guests and topics are just as compelling and timely from Ford CEO to NASA's administrator to the lessons from The Devil Wears Prada.

It takes about 10 seconds to find, just search rapid response wherever you listen to podcasts and hit follow to make sure you never miss an episode. I hope to see you there. Humans will never be more intelligent than AI. Those were great at AI and those that went out of business because they weren't. How do we build a future? That is human centered.

I'm Rana El Kalyubi. And on my podcast Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future. And we take you behind the scenes of the AI that's transforming our lives. Find pioneers of AI wherever you tune in.

So how can you tell a truly bad idea? From a bad sounding idea. How can you be sure your ugly duckling? could become a swan. This is the key.

You have to pay attention to the quality. Not the quantity of rejections. You want to see at least a teeny minority investors squirm. You don't have to get them to a yes. But you should detect some fiction.

As they reason their way to a no. Tristan has a keen ear for this quality in his conversations. He can pinpoint Down to the PowerPoint slide number. The moment his audience stops paying attention. Yeah.

I had a slide in there, I think it was like slide fourteen where I talked about proactive, the acne system. as like a um kind of a good analogy to what we're trying to do. You know, it's the difference between kinda Gillette and Bevel as like nutrogen and proactive. It's a system, it's all very important issue. And this VC looked at me and I'll I'll never forget this. Said

Tristan, I'm not sure issues related to um raise and bump shaving irritation are as profound and big an issue for people as acne. At which point I said, you know, I I kind of understand what you're saying, but all you had to do was get on the phone with ten black men and eight of them would have said this is a permanent thing I have to deal with. All you have to do is get on the phone with ten white men and Four of them would have said the same thing. Could have done it for women too, and you would have got the same ratios.

So it wasn't that it was like a bad idea or not as important. It's just that that person was unwilling to acquire the context necessary to understand what we're working on. That's just laziness. And at that point I can't fix that. So I just gotta move on until I find somebody who understood it. Notice how quickly Tristan's mind moves on to the next investor. When the quality of the questions drops.

He knows mid pitch. That the conversation's over. The rest is noise. Those half hearted questions are like the elevator music of the pitch process. It's meant to pacify entrepreneurs.

In fact. It greats at them. It also wastes their time. Tristan will tell you he prefers a hard no To a comforting.

Maybe. I mean, Silicon Valley investors will tell you all the time. We want to invest in people who can execute with some symbols of pedigree, chasing a significant white space and a big opportunity. For us it was like check, check, check, check. And we heard 99% of those.

Like how much is Right. And you just like Trying to say something that I want to hear as opposed to telling the truth. And I wish that Silicon Valley would tell the truth a little bit more. Tristan raises a really interesting question here.

How much of this investor hemming and hawing as well bullsh. So what's really going through their heads? As a partner at Greylock. I wanna share what happens. After entrepreneur leaves the room.

And investors left them all over. Crazy idea. It begins with a debrief of the investors partners. If I'm presenting an idea to my partner as a graylock, And they all go, that's great, we should do that.

I'm Mike. Sh Here's a bunch of hyper smart people and no one's saying, oh watch out for this or watch out for that. It's too easy. The idea is so obviously good, I can already hear the stampede of competitors.

Trampling over our hopeful little startup. On the other hand You don't want every person in the room to say Read. You're out of here.

Mine. Because then you're wondering. Hmm. Am I drinking the Kool-Aid in a very bad way? What you want.

Is some people going You guys are out of your minds. And some people going, I see it. You want a polarized reaction. So take my decision to invest in Airbnb as an example.

David Z told me during the Airbnb debrief David Z is a partner at Graylock Investment. Well Every venture capitalist has to have a deal that doesn't work. that they learn from.

Airbnb can be yours. And David Z is a super smart VC. He invested in LinkedIn. He invested in Facebook. He invested in Pandora.

He personally returned two and a half billion dollars to Greylock's buns. He's as smart as smart money gets. And believe me, I weigh his objections carefully. If someone as smart as David disagrees with me, I worry. But I also get excited.

It's an emotional roller coaster. And as this sort of emotional turmoil plays out in the background discussion, It's hard to give an entrepreneur. A hard no. The best ideas make you want to say yes and no in the same breath.

This mixed reaction can strain the relationship between investors and entrepreneurs. To give you one point example. My friend Josh Coppelman. the founding partner at First Round Capital. tweeted a picture of a letter he received from a Spurn founder.

It was a message printed in huge black letters. The sender who will remain anonymous wrote Dear Josh. We'll see. I think you've already fed yourself over by getting left out of this deal. Josh commented on his tweet.

Well that's one way to respond when a VC passes. But I talked with Josh. And that tweet doesn't even begin to capture the full range of emotions he experiences when he turns down a founder. So um but why did like just kinda personal question. Why did you tweet the letter? What was the impulse? It wasn't to mock him, it was just to almost

Show that I recognize I have a privileged life just because I say no, it doesn't end there. It's a hard thing, you know, I'm an optimist, you're an optimist. The job is ninety nine percent of the time we're saying no. And so when you become a VC, you have to try to figure out

Like what style? But I've actually found that when you're going to pass being able to be explicit and transparent about it And also doing it up front. Probably same experience you had when I was raising money, there were three types of VCs. My favorite with a quick yes.

My second favorite were the quick no. And my least favorite was the long drawn out, maybe if you show me this and prove this, I knew that I wanted to be in class one or two. And that's what I optimized for. Yeah, quick yes or quick no. Well and the problem with the type three of E C is actually they're damaging the founders. And they're really just trying to play out their own image. You know, their own option on this. That's exactly right. Why say no? I'll just wait around the hoop and maybe if something changes, I'll get a shot in. It is very damaging for a founder and and many founders, because they're optimists, they have happy ears, they hear that as oh this VC is interested when what they really should be doing is just saying, Thank you, let's move on to someone else.

Now, on the other hand, I've got quite a long woa coulda shoulda list, so there you know as I tell most founders, um There are plenty of companies that that are in that anti portfolio, so Um you know, I'm often wrong. Are there any particular founders that you passed on that you're haunted by? Yes. I mean I try not to obsess because the list is so long.

I like the way that Josh describes his list of missed opportunities. Every VC, including me. has a list like this. An anti portfolio. The startups you might have funded.

Which cast a long shadow over your conversations to entrepreneurs. And if you as an entrepreneur. See a flicker of that shadow cross an investor's face, that should give you comfort. Ultimately, you need to get used to being a lone champion. And there's a question Tristan poses to himself.

Which is a good question for every entrepreneur. Who's in the depths. of a grueling pitch process. What do you fundamentally feel that you're the best person in the world to do? And like really be thought about that. you know, increase your humility a little bit and really think about what you're uniquely qualified to do.

And then two chase the bad ideas. Like it may be that there is a hundred thousand people. Who could go solve this problem? If they knew about it. If they're motivated by it.

But of those hundred thousand, you may be the only one who knows about it. can assemble the resources and wants to do it. One of my favorite quotations is from uh Robert De Nier in the movie Ronin, which is If there is a question, there is no question. And the parallel in entrepreneurship is if you do not have an absolutely solid theory of competitive differentiation, you do not have competitive differentiation.

And it's really important to have competitive differentiation. For example, if you said at the beginning of LinkedIn, what was my differentiation? My differentiation is I understood virality. Am I an expert on careers and the job recruiting marketplace and hiring? Like, no. Right. I'm the unique perfect person doesn't mean that when you line up every attribute, you turn out to be the only person. It's the action fact that you're taking a unique shot and you have a unique ability to take that shot relative to competition. And once you're certain of your competitive advantage, you'll no longer feel like you're waging a quixotic battle against conventional wisdom. You'll feel like the world must eventually come around to your way of seeing things. I think health and beauty is doomed for all types of reasons I could suggest and talk to you about. But one in particular, um

really sticks with me and still does to this day. Yeah, I think all global culture is led by American culture, which is led by black culture in the US. And more recently in C Asian culture. The big frustration of mine is my living in the early subdupting region on the planet. And it's knowing very little about the earliest adopting culture on the planet.

Right, like that Discord doesn't make Too much sense to me. So I'm trying to show folks that Here's one of these kind of lost industries that have seen no disruption. Certainly with technology.

have seen no disruption, certainly with like this demographic group that I understand and the cultural impact of it. Uh, you start to see, you know, this demographic group becoming the majority of the country with increasing wealth, access to technologies, the early adopting culture on the planet. my experience of not having products that work for me, my ability to potentially raise money for that thing. I don't think there's anyone better on the planet to do this one thing than I. And the day I came that realization, it was the most freeing moment for me. And I didn't care about hearing the nose anymore, because I knew that we had something. I'm Reed Hoffman.

Thank you for listening. Masters of Scale is a Wait What original. The show is recorded on site in California and produced at the studio inside SY Partners in New York. Our executive producers are June Cohen and Darren Triff. Our producers Jenny Cataldo. Dan Kedney and Ben Manilla.

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