Raise more money than you need, w/Minted's Mariam Naficy

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It's nineteen ninety eight. At the height of the first dot com boom. Silicon Valley's on fire, nothing bad can happen. My friend, Merim Nefisi. is CEO of a startup called Eve, and she had to have the domain name Eve.com.

Only problem? She has to convince the owner to sell it to her. And she was facing a negotiation. That I do not end it. Hello, who is this?

Eve Rogers. Who gets on the phone. So I think, what on earth am I gonna say to this five year old? So I said hello. Hi. Could I buy Your domain name. And she was just saying to me.

What? I don't really understand. Um what? And I'm sure Eve's mom on the other line was laughing her head off. I mean, this is a great joke to play on this, like silly entrepreneur from California who's calling her like just I'm just gonna like watch her be tortured by my five year old for a while. Meram turns this risky negotiation over to her lead investor, the legendary startup whisperer Bill Gross. So he gets on the phone with her mom and he negotiated the purchase. And it was um No, equity in the company, a board seat for her daughter, a observer board seat. Trips to Idea Lab to see Bill several times. A year. You had a five year old observer on your board? Yes. She didn't actually show up for the board meetings, but she did occasionally come by and visit. Disneyland. Software, educational software. I mean there was a very large package that was negotiated.

If you were gonna call your younger self. How would you have handled this negotiation differently? I would probably throw in the Disneyland almost immediately. I have a daughter and I would have said How many times a year do you want to go to Disneyland? Once a year, twice a year. Maybe about a hundred times a year. Exactly. Fifty thousand dollars plus Disneyland trips may seem like crazy expenses. But my experience Every successful founder has a story like that.

You gotta have incredible talent at every position. There are fires burning when you're going out. 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. Oops. Or do we have a three-bedroom apartment? We haven't made it. Just how you do it. This Is masters of scale.

I'm Reed Hoffman. Partner Greylock. co-founder of LinkedIn and your host. On this episode, I'm gonna make the case that as an entrepreneur You need to raise more money than you think you need.

And potentially a lot more. I'm gonna prove that theory through conversations with some of the smartest people that I know. So why should you raise more money than you think you need? One word. Disneyland.

Marim Nefisi did not imagine that she'd spend over fifty thousand dollars buying a domain name from a five year old. She certainly didn't imagine she'd have to sweeten the deal with tickets to Disneyland. But that's life as an entrepreneur. If you look at a typical startup's budget and sort the line items by sheer strangeness, How many expenditures would fall outside the limits of your imagination?

More than you think. So you have to plan paradoxically for the unknown. And that's the first reason you should raise more money than you think you need. But there are more reasons, and you'll hear them in the story of my friend Mariam Nafisi. Merriam has weathered booms and busts. She's one of those rare entrepreneurs who succeeded through the first dot com boom and the second internet wave.

Her story is a pretty convincing case for grabbing as much capital as you can while you can. We'll start with her first company, Eve.com, which back then sold cosmetics online. It was the height. of the dot com book I opened my doors at Eve.com and we had literally orders coming in that very day. We're like sitting there watching orders pile in for cosmetics and all kinds of cosmetics that we didn't think we would sell online, like color cosmetics, things that you think you might have to try on. Just success immediately.

Immediate success of twenty eight. We were able to raise$26 million in the first year. So we did a very fast scaling of the company. I think we went to from zero to 120 people in six months. I think we'd hired the entire what they called C suite of executives within six months. Can you believe it just like an entire executive team, poof, overnight in six months. So when Miriam was describing her instant exact team, I had three emotions all in one bundle. Panic, calm, and acceptance. Panic?

From the viewpoint of oh my gosh, that's gonna be a train wreck. Calm because early days LinkedIn, I did something similar, but of course I did that with all people I knew. And then acceptance because the classic part of the entrepreneurial journey here is being in permanent beta. You have to be always a work in progress and trading. And in nineteen ninety eight, everyone was a work in progress. Most Silicon Valley startups are spending and hiring at a blistering pace. Merham did exactly what any sensible entrepreneur would have done.

She raised as much money she could, and she moved fast. She went all in. I think the thing was that the market was so heated and so many VCs were backing competitors in this space that I had to raise it was good that we raised that much and got out ahead of everyone because we ended up in the number one spot. And five Venture Back Beauty companies launched in after us. We were running TV ads. It was a complete uh land grab. Miriam called it a land grab, and she was right.

Everyone used that language. Land grab. And even Gold Rush. And in that kind of heated market. you have to raise a lot of money because your competitors are raising a lot of money, after all.

You're trying to win. It's easy to err on the side of caution. To raise less. And to spend less. But there's a potential moral risk in being conservative.

You might think you're best serving your investors by being as efficient with capital as possible. But that's actually not true. You award your investors by creating a successful company. And raising only twenty million dollars might mean losing the twenty million if your competitors outspend you. Now Mariam raised twenty six million dollars and it kept her one step ahead of her competitors.

If she could have raised even more, she would have. But is there such a thing as raising too much money? Personally, I don't think so. But let's hear from someone who does. My friend Selina Tabakowala co foundered Evite

An online invitation service. Around the same time that Merriam founded Eve.com. Selena went on to serve as president of Survey Monkey. And is now founder of of the new startup. Kick so

I asked her to reflect on the money she raised for Eite. We took way too much capital. We took$37 million in the end for online invitations. Like it sounds crazy, it was crazy. At the time it was all about get the eyeballs, put a beltboard on 101. Like it was spend the capital higher, higher. And the thing I've learned, make sure you have a strong business and then scale it out. Make sure you have the right unit economics, make sure you have the right fundamentals. And there was no reason we should have taken so much capital. Selena looks back on the thirty seven million and says, Wow, that was kinda crazy. And it does seem crazy. But that's the market you're in. You have to play to win, just as your competitors are playing to beat you.

You have to be the last person standing. The truth is thirty seven million in Silicon Valley seems kind of average. Or even on the low side today. The amount of capital going into these companies has been growing. It's worth the risk, because if you succed.

You create something spectacular. And Miriam is in full pursuit of the spectacular at Eve dot com in nineteen ninety nine. Working till ten o'clock every night, like seven days a week. She's flush with capital, having raised more than she thought that she needed at the time. And then The bubble burst. And this was a very dramatic moment for those of us who lived through it in Silicon Valley.

Companies were going under every day. There's this website devoted to covering businesses that are failing. I won't tell to say the name of it. I think we can, although maybe they'll let it out, which is obviously f company. Exactly. So everybody's looking at it every day and the Wall Street Journal's reporting and New York Times. So it looks like the world from a young twenty nine year old's perspective, your whole world is basically imploding and the internet is over, basically. The internet is over. It may sound like a punchline, but back then people really believed it. And the right response was actually, no no, the internet is huge. It's still coming.

This is actually precisely the time to bet on a dot com company. I was personally lucky. Because I was an executive at PayPal and we survived and in fact thrived through the dot com crash. But I also read f Company. I knew the entrepreneurs splayed across its pages. And those stories have a funny way of sticking with you.

As for Miriam She sold her company just in the nick of time. I get my investors hold. They've all made money, basically. I have made money. I at this point am feeling a sense of relief slash exhaustion at the whole roller coaster I've been on. So I think at this point I just really wanted to get away and exit and just leave San Francisco for a little bit. Mm.

And on top of the exhaustion. There were unexpected consequences. We worked really hard on Eve dot com and we made the right ultimate decision at the exact right time. So that's good. But we were often called fortunate and lucky, which we were. And then when the whole thing came crashing down, there was so much resentment that had been understandably built up around these young entrepreneurs who had so much money to spend. that there was a huge backlash from everyone.

They were like, Thank goodness these people have been shown a lesson, right? And so you basically went from being someone to being absolutely no one and shunned, and it was really humbling. Was there a particular uh experience which suddenly represented that shift from being in this kind of golden spotlight to being completely shut. Yeah. Yes. All the agencies that would call on us at Eve that always wanted to get to know you as a CEO or make your friend or your acquaintance and and help you they all just basically overnight turned off. The relationship just turned off. and there was like n absolutely no receptivity to anybody among the headhunting firms, for example. it was very much the opposite of welcoming. And so that was really you know, that was really humbling.

When Marion was reflecting on her transition from being a grand poopah Somebody important. To being a deliberately ignored nobody. It made sense to me.

It's a very human reaction to worry about how people look at you. But you can't let this paralyze you. When I consider investing in someone, I look for founders who will risk almost everything. including notably their reputations, in order to succeed. Mariam now runs the risk.

Of not risking enough. And I saw a banker after this who was much older than I was and he was like your biggest problem of life From now on is that you're going to be too conservative. I anoint you, therefore your curse. Your curse is that you will be forever too conservative. This idea of the conservatism really stuck with me.

A week later, I was thinking about it in the car. Yeah, when Miriam was commenting on our own curse of conservatism, the incentive being not to risk that and to make it look like it was just a fluke or mistake. It made me kinda think about who are the people that I see Who also, you know, end up playing that way. Why do people risk it? Why do I risk it? A lot of people risk it because they they're still hungry, they have something to prove.

lot of people risk it'cause they're kinda risk blind, they just don't see the risk. I can think of people in each of these categories. When it came time for Mariam to launch her second company, She didn't want to take a lot of risk. She wanted what's known as a lifestyle business. The kind of business that's predictable and fairly safe is

With a steady stream of revenue that supports a comfortable lifestyle for its owners. No big risks. No crazy drama. At least that's what she thought. This time I was I said to myself, let's not bring in all the V Cs at the beginning. I know uh what I'm doing this time, so I chose no co founder this time.

No V C at this time. Let's figure out how to build perhaps a sustainable lifestyle business, cash flow business, is what I was thinking in the beginning. If Miriam and I had known each other from when she started Minted, I would have actually told her, abandon that theory from the very beginning, because it's really not gonna work. So called lifestyle businesses are very stable and reliable, and technology companies just don't behave that way. They need to move super fast and they need to be able to constantly correct and pivot. They need to be able to perform the twists and turns of fighter plane combat.

Tech businesses absolutely need to raise more money than they think they'll need. They'll need that capital for all of the unknown pivots, whether it's new customer needs or competitive attacks. To show you this difference between lifestyle businesses and scale businesses like tech, I wanted to talk to the classic kind of entrepreneur. The kind I usually don't get to work with. Like almost kid me.

He's the proud owner of the wine and cheese place in St. Louis. And he knows his business model. He also happens to be our producer's dad. Cheese place. I don't.

Are you ready for a big interview? Sure. Are you nervous? Are you kidding me? So it's just a simple math question.

Mm-hmm. If we were to open another wine and cheese place. How much would it cost? Roughly four hundred thousand. You don't have to pull up a spreadsheet or anything. No, I've been in that game for so long, I know.

Pretty closely what it takes. You have to understand that our type of business is pretty stable. It's almost as stable as supermarkets. The parameters are known the risk is low and that's why when you observe you see that not too many supermarkets go under. They may be more profitable, less profitable, but They are not going under the rate that someone like, say, in the fashion business or in the software business. But Silicon Valley is not the place for you.

Silicon Valley is a wonderful place to live in, but I won't put the nickel there because I don't have the guts. Mm. Perhaps Silicon Valley's made me an adrenaline junkie. But I actually kinda look at certainty as somewhat boring. And that's the sort of certainty Marim is craving as she launches what she thinks will be a lifestyle business.

We'll head down that winding path with her in a moment. But first, note that Marion's life had changed between her first and second company. So I had become a mom in between. So I'd had my son and I just was having my daughter when I came up with this this sort of lightning bolt struck. So Being a mom and an entrepreneur the second time was really difficult and challenging, but also I also felt like other people probably anticipated it being too challenging and they do write you down a little bit. If you're a mom and you're pregnant and you're starting a company versus if you're a young 28-year-old entrepreneur starting a company, there's significantly different ways in which you're treated, actually, as an entrepreneur. Which is terrible. Yeah. And you are the perfect kind of example of why that's an actually even a dumb idea, let alone an immoral idea. I think I got seriously discounted despite the experience of having a successful exit for people.

I said this in the room, but I have to say it again. The idea of discounting entrepreneurs who have families is ridiculous. Investors need to let go of it. Back to Maryam. My f my close friends and acquaintances knew that I was good. My angel friends said

We believe in you. Screw it. We're giving you two and a half million dollars to start Mintis. So I did there was a significant upside from having delivered successful exit. When you've built 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 plating dot com slash masters of scale. Humans will never be more intelligent than AI. Those are 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 Calyubi. 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. 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. And so Merriam launched a new business, Minted, an online stationary store, not so different from an upscale neighborhood card shop.

She stocked up on cards from brand name companies, but Minted also included a daring little side experiment. Merriman invited unknown artists to submit designs to an online competition. Anyone could participate. Anyone could vote. The winners would then compete head to head with the heavyweight champs of the card industry.

And so in two thousand and eight. Marin was ready to release her slightly offbeat selection of Stationary to the World. Here's what happened. I opened the doors. There's not a sale for an entire month. Nobody wants the branded stationary products that we'd spent most of our two and a half million launching'cause again, being conservative, I'd said, I know, I'll do a Neve.com, I'll put all these brands online. Sign'em up exclusively. We had exclusive distribution rights. Nobody wanna buy them at all.

Instead, the teeny weenie assortment that I had sourced through this one competition I'd run one transaction a week. Then the next week there were two. We had sourced 60 designs through a competition and I'd saved a tiny bit of money to build what I really wanted to build. Out of the two and a half million, I s probably spent like a hundred thousand on what really became into it was this like little side thing and there was a programmer up in Oregon and he and I were working at night on building the first competition. And that is the only place where we saw any sales movement. Marion stumbled under the power of crowd sourcing.

The idea that ordinary people When they come together in large numbers, can do work once reserved. Only for experts. Etsy is an example of this. Kickstarter as well.

But at this point, in two thousand and eight, it wasn't understood very well. It was something Silicon Valley was just getting its head around. I realised that this crowd sourcing thing was way different and I'd uncovered something that was more of like a massive social cultural change going on in the US and and maybe in the world. versus just some small business idea. Because what was happening that I didn't realize was that

who's considered a creative out there is actually changing a lot right now due to technology and exposure. And so people are emerging as creatives who n haven't gone to school. They haven't gone to design school. They haven't gone to art school. And they're d massively disrupting art and design right now. And there is a meritocracy, a true meritocracy that you can actually build and unleash. So our sensible lifestyle business has nearly collapsed. There's only a teeny sign of life in a funky little crowdsourced marketplace, a place where amateur designers sell cards to adventurous shoppers.

It's new, it's different, and aside from a trickle sales, there's almost no evidence it'll work. There's only one certainty at this point. Merriam needs money, a lot more money. We're about to shut the company down. I thought, you know, I could take whatever's left of the capital and just give it back to my friends. I cannot lose the money of my friends. I was maniacal about that. Like these are my friends, it's terrible, hundred thousand, two hundred thousand each, this is gonna be really bad, I gotta give the money back. But then when I saw started seeing these little bits of sales and my true lead angel he said, You know, I think that you need to save the company potentially by considering venture capital. And he's like, I think you should potentially consider a raise. And I started seeing signs of life too. So I said

I can save this company and I can get the money back to my investors. I should do that. Reputation's everything. I got I wanna I wanna do this. So the venture raise was primarily triggered by I have to make sure I deliver to the Angels. Yes. So basically the only reason that Miriam did a round of financing was to pay her friends back. I was very much driven by a feeling of obligation and loyalty to my friends. And so I raised the venture thinking that I would then save the company and then somehow deliver the money back. Not because I really wanted to raise venture. Here. Miriam runs into another reason you need to raise more money than you think you need. Unexpected opportunities.

Marion's plan to start a lifestyle business just didn't pan out. She didn't have enough funding to cover plan B or her plans B, as I like to say. Opportunities may arise later than you hoped. And you want the capital. To carry you in new directions.

So she reluctantly pitched her idea and secured another round of funding. And if that weren't risky enough, she's about to encounter one more familiar source of uncertainty. A stock market crash. And we raised our venture around two weeks before Lehman failed because this investor of mine had said to me, I feel something really bad's gonna happen, you should go raise. So we just went out August. Who's in town? Anybody? Anyway, is anyone in town in August? So we went and raised money. It closed it literally right before Lehman failed. We're down one point seven percent here. Dow at the same time has fallen about eighteen percent. Experimental business idea into the heart of the worst economic crisis since the Great Depression, the collapse of the US housing market in 2008.

Suppose she'd waited until, say, September to raise that money. Lehman collapses, panic groups investors, and no one in their right mind gives cash to a bold little experiment in crowdsourcing. Like that. Minted closes for business. Which is another reason you should always take the money.

Whenever and wherever you can get it. You never know when it will dry up. As it is, Merriam did raise the money. And she still has to create a thriving company. So first she has to figure out what her customers really want.

I want to take you into the heart of Merriam's grand experiment. When you're launching a truly disruptive business Questions don't lead to answers. They lead to still more questions. Questions you hadn't even thought to ask.

You put a product in front of a customer. Their reaction surprises you. You go back to the drawing board. You return with an improved product. Your customers surprise you again. It's a bit like a mad scientist desperately trying to prove a hypothesis and running up the budget in a lab. So I do a lot of my own focus groups myself.

with customers. I moderate them. I write the scripts still a lot. I love to talk to consumers. And I do that many, many times a year. People are really shocked when they come in. for Focus Group and the CEO is moderating. But I love it because I'm listening very carefully to find little tiny nuggets of insight that I love collecting. Is there one particular nugget from one of those focus groups that comes to mind? Oh god, there's so many. Like making prices all equal for different kinds of paper and realizing the analysis paralysis people went through. You like almost had to give them a reason to make a decision just by changing the price. Well, that was just fascinating. I realized, for example, talking to people who buy art that it really depends their their art decisions depend a lot on like whether they buy a home or which home they're on, frankly. Are they on the first home, second home.

You know, the Gen Xers were telling us when we started the company they didn't care who made the design. Flash forward five years later, they're probably like, why aren't you telling this story more? I need to hear about these artists. Like, what's going on here? We're in the middle of a cultural shift. Millennial men like to be involved in the wedding decision with the millennial woman. They're more involved dads and they're more involved husbands, actually it turns out. So we learned that our designs were too feminine in weddings and you wouldn't necessarily even know to ask that question. And that's the problem with building a business that has no blueprint for success.

You have to anticipate false starts. You design cards for brides and then realize grooms are the ones buying. You give short shrift to their artists' profiles and then realize millennials want their whole life story. Here's the lesson. Your customers are always a bottomless well of surprises.

How do you budget for an experiment on this scale? Miriam has a simple rule of thumb. In those early years when there was little access to capital, we had to be really cash conscious. Things are always more expensive than you think they are and they're always gonna take more time to prove out and you're gonna need more optimizations and more loops to correct things than you think you will. That's why we just say, roughly speaking, it meant to act like you've got half because you've gotta like factor in all the failures and all the optimizations that really kill great entrepreneurs and businesses all the time. I mean, we know so many people, both of us probably who were People who had good ideas were on the right track, but they just ran out of runway.

I want to point out something here. Marion was an investment banker. She can crunch numbers and budget with the best of them. But her rule of thumb, spend half, is not quite an exact science. Will twice as much money keep the experiment going?

Why not three times as much? Why is it so hard to accurately predict costs? In fact There's an academic term for this. Call the planning fallacy.

That's Daniel Kahneman, genius Nobel Prize winner and one of the leading experts in our budgetary blind spots. We asked them why this so called planning fallacy exists. And what it means for different kinds of entrepreneurs. And the planning fallacy is that you have a plan and then you get the resources that are needed for the plan with a little bit of modular safety. But most plans fail. They fail dynamically.

The way to overcome it in part is that and it's implemented, by the way. There is something that actually I invented it and I call it the outside view. And so when you have a problem, you look at the range of similar problems and you look at the statistics of what happened. And in particular if you look at the statistics of over of override and they're different for different types of projects. No. familiar projects like building another house or things like that. The overruns are small by and large. But the more unfamiliar the project is, the bigger the overruns on average. The kind of entrepreneurship that I pursue and frankly is the kind of entrepreneurship Silicon Valley pursues

Almost always is something new. Right. It's almost always a new game. It may be a new game because the tech platforms are different. It may be a new game because the competitive landscape has changed. It may be a new game because there's an anticipation or a fact of an opening up of a certain form of market demand or consumer demand. So almost always you really have no clue. You're throwing darts at a dartboard about how it played out. The jump into the unknown where you're like Who knows is at least a certain adrenaline rush that perhaps I'm over addicted to.

My own worry is that certain areas that I get too expert in, I then become a bad investor. Because I'm too aware of all of the landmines. So for example, at Greylock Because a PayPal, I'm the payments guy. I haven't really done a payments investment yet at Greylock, because every time I look at them, I think back in terms of the literal huge landmine field that PayPal ran through. And oh my gosh, I'm aware that there's explosives all over the place. And it makes me too conservative for making bets that I otherwise should make because You know, there are some great payments companies out there, Stripe, Square, et cetera, that I talked to very early and couldn't bring myself to kind of lean in to do, despite world class great entrepreneurs. Note to self mistake. Right. Because I was going, Oh my gosh, I know how bad this hit payments area is.

So that's my curse is kind of a curse of knowledge versus a curse of conservatism, which may lead to making bad risk bets in some selected circumstances. So I feel that I fail and I still fail every day, several times a day. It's just that you hope that you have enough successes that outweigh the failure. It's just completely normal and it's something that I think hopefully everybody could talk about. There's an important postcript to Miriam's story.

She raised eighty nine million dollars in venture capital for Mitte. Which is now a nine figure revenue company with three hundred and fifty employees. They've shipped products to 70 million households around the world since she founded the company. By now, you have the sense for my theory. Entrepreneurs need to raise a lot more money than they think they need.

But every good theory has a counterpoint. For this, we'll turn to my friend Brian Chesky, the CEO and co-founder of Airbnb. I think startups raise way too much money. The less money you raise, the more control of the company you keep, but more importantly, the more constraints you create. They develop a scrappy culture. The scrappy culture requires you to build more novel solutions, use fewer out of the box software things, and you end up just building a scrappy, more frugal, more startup like environment. I would make sure that you give away control grudgingly.

So Brian would take my advice cautiously. But cautiously or not. There are a lot of important reasons to raise more money than you think you need. To respond to unexpected expenses. to outmaneuver the competition.

to guard against economic downturns, and to take advantage of opportunities that may unfold late in the game. The only thing you can do is set aside the uncertainties and just know the failures will come. Budget like you don't know when they'll stop. And each time you're walloped by some unexpected expenses,

Remind yourself. It's normal. I'm Red Hoffman. Thank you for listening. Masters of Scale is a Wait What original. Our executive producers are June Cohen and Darren Treff.

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