identify pain points and know your audience : Planet Money : NPR




That bell can only mean one thing. It’s time for PLANET MONEY Summer School. Whenever the temperature rises and the beach beckons, we show up with a batch of easy lessons to make those lazy afternoons a wee bit more productive. In summers past, PLANET MONEY Summer School has taught us to think like an economist and invest like a boss. This year I think we’re ready for graduate school – oh, yeah – a master’s in business administration. An MBA the easy way – I should trademark that. I’m your host, Robert Smith.

Now, some might be thinking, Robert, I don’t want to spend my precious summer doing hostile takeovers of underperforming businesses. I want to fire up my barbecue, not fire all my workers. Why do I need a cut-rate MBA? Once upon a time, I thought the same thing. I’m a reporter. I teach journalism at Columbia. And yet I got an MBA. And I found that what business school does is very similar to our jobs here at PLANET MONEY. You try to understand the nuts and bolts of how a business works – the principles that drive this fierce competition for our attention and our dollars. And business schools even use a very PLANET MONEY method in their classes. They read case studies – little stories about someone trying to start a business, their challenges and the decisions they make. Our season will work the same way. We’ll play classic PLANET MONEY episodes as case studies. We’ll hear from business geniuses…

P J MCGEE: The most insulting thing we hear is someone says you’re a natural born salesman. Well, screw you. I spent a lot of time and effort to learn how to do this properly.

SMITH: …Fierce competitors…

STEPHON MARBURY: Oh, you’re going to make all of that stuff for $15? Damn.

SMITH: …And expert negotiators.

CHRIS VOSS: You know, the real trick to bargaining is get the other side to bargain against themselves. You just lay back and let them do all the work.

SMITH: And then we’ll bring in a fancy-pants business school professor to give us the fundamental principles we can all use in our lives.

ANGELA LEE: Accounting is your superpower.

SMITH: In today’s class, we will start our MBA degree from square one. What are the very first steps someone needs to know when starting a business? Our professor is Angela Lee from Columbia Business School. She’s been an entrepreneur. She teaches future entrepreneurs, and she runs a venture capital firm, 37 Angels. That means she’s been pitched 20,000 business ideas and invested in about 100 of them.

LEE: So I’ve been pitched everywhere. I’ve been pitched in the restroom. I’ve been pitched in line at the grocery store. I was once pitched in a restaurant by somebody who was sitting at the table next to me…

SMITH: (Laughter).

LEE: …’Cause they realized who I was.

SMITH: I admit it – I was totally going to pitch you my million dollar business idea. But instead, let’s just talk about starting a business. We always think of entrepreneurs as these lone geniuses who break all the rules. But can you actually learn the rules of starting a business?

LEE: I think you can really learn what not to do…


LEE: …In terms of starting a business.

SMITH: Yeah.

LEE: I think you can learn – don’t use this social media channel to acquire customers. Or don’t use this subject line in your email. And I think that can save you a lot of time – save you a lot of bashing your head against a wall.

SMITH: Cautionary tales.

LEE: Absolutely.

SMITH: Well, we will listen to two – well, I won’t call them cautionary tales. They’re interesting tales, and maybe we can talk about the principles that we can learn from them afterwards.

LEE: Sounds great.


SMITH: OK, our two case studies today feature people starting new businesses in the most challenging conditions you can think of. And if they can do it, you can do it, too – after the break.


SMITH: Welcome back to PLANET MONEY Summer School. We wanted to start our MBA class with a story about how ideas for new businesses can be found in the places you least expect. As you listen to this case study, think about where entrepreneurs get their ideas from and how they test out those ideas to see if anyone wants to actually pay for it. This story originally aired on PLANET MONEY in 2015, hosted by me and Steve Henn.


STEVE HENN: Frederick Hutson had this entrepreneurial itch pretty much from the day he was born. In high school, he had a lawn-mowing business where he got other kids to actually mow the lawns. He did the same thing with a car-washing business.

SMITH: The guy was a natural. He went to the Air Force, moved to Las Vegas, started a window-tinting business. And then he bought a mailing center – one of those off-brand UPS kind of stores – in Las Vegas. And this store was key to his biggest business plan yet.

HENN: He was going to deliver marijuana all over the country using UPS and FedEx.

SMITH: What could go wrong?

HENN: What could go wrong?

FREDERICK HUTSON: I’m at the mail center, and I’m just sitting behind the counter. And then I see – it’s, like, all glass. And then I see agents coming from both sides – about 12 people from both sides – and they just all, like, rushed the door – like, with guns drawn.

HENN: Frederick got nailed for conspiracy to distribute marijuana – five years federal prison.

SMITH: Now, some guys go to prison and they find religion. Some guys go to prison and they work out a lot, get massive biceps. But remember; Frederick Hutson was the businessman. So he would spend all of his time in the prison library, writing business plans.

HUTSON: So I just spent every day writing random – whatever I did – even if it wasn’t even possible, feasible, I would just write a plan for it. I would write how I wanted to build it. I would write who I wanted to hire. I met white-collar guys, and I would – they showed me how to write financial models. And we would get paper, tape them together – white paper like that – get rulers, and draw lines and make spreadsheets by hand.

HENN: Like, physical paper spreadsheets.

HUTSON: Right, right. Yeah (laughter). Right? So it was a tedious process, but I had time to do it.

HENN: He was doing what entrepreneurs do, right? He’d pick a problem and figure out a solution. But as the days went on, Frederick realized the biggest problems that needed solving were actually all around him, inside this jail.

SMITH: Yeah. The first thing you notice in prison is there is no competition. If you want to buy soap, there is only one place to get it – the prison commissary. And it is way overpriced.

HENN: And Frederick says that’s nothing compared to the payphones. I mean, those guys can charge whatever they want.

HUTSON: Basically, when I was in the county jail, I was making calls out, but it was expensive. It was getting to the point where Tanya (ph), who was my girlfriend at the time – she was like, I can’t afford it. Every time you call me, it’s $50. So I stopped calling as much.

HENN: Wait. Every time you called her, it was $50.

HUTSON: She would have…

HENN: How long were you talking?

HUTSON: Right. We was talking – I think the calls were, like, 15 minutes. And what – the reason why it cost 15 minutes…

HENN: Fifteen minutes for $50?

HUTSON: Right. It was very expensive.

HENN: The phones are a drag. But the thing that really drove Frederick nuts was this photo problem. He wanted his girlfriend to send him a photo, but inmates aren’t allowed to have cellphones or internet access. So for his girlfriend to actually send him her picture, she’d have to go and print it out at a drugstore, put it in an envelope and mail it to the prison. And that didn’t happen.

SMITH: Fredrick lies there on his bunk, mulling over this problem. And then he goes to the library with his blank pieces of paper and pencils, and he starts thinking about the photo problem like a businessman. What if there were a company that could make this whole photo thing easier – a website or an app – some technology that would allow someone to take a picture, hit a button, and then, poof, that printed photo would automatically get sent by mail to prison?

HENN: So this whole idea basically started because you wanted to get pictures from your girlfriend, right?

HUTSON: Right.

HENN: Forget pot delivery. This was going to be his perfectly legal million-dollar idea. He even came up with a name for it, a kind of 2010 name – Picturegram.

SMITH: Picturegram. Now, there wasn’t much he could do about building Picturegram while he was still behind bars. But when he got out in September of 2011, he brought all those business plans he had developed with him, all those paper spreadsheets and smudged lines. And he headed out for – OK, normally, if you’re a tech entrepreneur, you would go to Silicon Valley. But Frederick was not. He was a convicted felon out on parole. His destination was a halfway house in Tampa, Fla.

HENN: And to hear him tell it, you couldn’t imagine a worse place to incubate a tech company. At this halfway house, every aspect of his life was controlled. He didn’t have the luxury of uninterrupted time in that prison library. He had to constantly check in or check out. And they kept saying, you have to get a job. And no, starting your own company – that doesn’t count.

SMITH: So he started to build Picturegram on the sly. Initially, his plan was to hire a couple of guys, put up a website, print some photos. So he calls this photo processing lab.

HUTSON: And he said, but, you know, well, we’ll set you up a call with the CEO and all his people. So then they set up this call – it’s my first conference call. I’m still living in a halfway house. And the million-dollar…

HENN: How do you take a conference call in a halfway house?

HUTSON: I had to sneak my phone in. So they had a rule, which is stupid, but you can’t have a phone. They didn’t let you have a cellphone. So I used to sneak my phone in. And I’ll be in my bunk, laying to the side, and on this conference call with our vendor and the CEO and the sales guy. And basically, I have to pitch him.

HENN: And you’re doing this while laying on a bunk…


HENN: …Speaking quietly in a halfway house…

HUTSON: With a room for probably eight other people in this room. So…

HENN: How did you make that pitch?

HUTSON: It actually came up because I told them – I said, I’m looking to build an app to allow people to send pictures. They wasn’t impressed by that. You know, there’s hundreds of those already. What are you going to do that’s different? And I said, well, we’re going after inmates. And there’s really no service that’ll allow people to send photos to inmates. And we’re going to be the first, and we’re going to be the best ’cause we have a unique way to market to them. And then he was like, well, how do you know that this opportunity exists? And I’m like, ah, s***, what am I going to tell him – right? – ’cause I’m worried that he’s going to say no if he knows that I’ve been in prison. But there’s no way for me to hide it ’cause I have too much inside information.

So I take the leap, and I tell him. I said, well, actually, I know because I did four years in federal prison for distribution of marijuana. And the phone was just silent. So I don’t know which way it was going to go. But then the CEO said, you know what? This is the most interesting thing that I’ve heard. Let’s do it. I’m excited about it.

SMITH: Frederick realized that this thing that he wanted to hide – that he was a little ashamed of – was also his best selling point. He knew the market. So Frederick teams up with an old friend and starts to raise money – a thousand bucks here and there from family and friends.

HENN: But, of course, this is really only half the battle, right? He spent all this time trying to overcome the barriers that being a convicted felon threw up in his path. But he still faces all the classic problems every other entrepreneur faces, right? Like, how do I reach my customers? How are they going to pay? Do people want this? Will it work?

SMITH: The only way they could figure this out was to try it. So in 2012, they built the website. They were ready to put out their first ad, get their first customers. But because this whole thing was aimed at prisoners, the whole advertising situation was pretty low-tech. They basically had a postcard, a picture postcard that they mailed out to 500 inmates, a list of inmates that they found on the internet somewhere.

HENN: The ad copy was pretty simple.

HUTSON: We said, someone wants to send you a Picturegram. And to have them send it to you, go to this website. And that was it.

HENN: Now, some of these postcards had a picture of a mom cooking dinner. Some had pictures of kids. Some had pictures of attractive women. But every postcard offered one free picture sent through the mail if their loved ones set up an account.

SMITH: So basically, it’s just junk mail.

HENN: Yeah, it’s absolutely junk mail. And, you know, a normal piece of junk mail gets a response of, like, 1%. So if you send out 500 postcards, you could expect maybe five people to respond. But remember; Frederick Hutson knew something most people don’t. Inmates love mail.

HUTSON: All of a sudden, like, two or three days later, all these orders started coming in. People started shipping photos.

HENN: Out of that first batch of 500 postcards, they got something like 135 paying customers. The response was just nuts.

SMITH: And it was sort of a revelation for Frederick because, all along, he’d been thinking about prisoners and the problems of being in prison, and he thought of the website as a service for inmates. But as he started to see these responses, he thought, no, no, no – of course – like, the real customers are the families. In all these responses, there are mothers and fathers and brothers and sisters. It means as much for them to be able to send a photo as it means for an inmate to get that photo. Frederick decided to pivot.

HENN: Frederick’s companies built this giant database of all federal prisoners in the country, and they’re using it to sell all sorts of services. They started a telephone service that gives families local numbers so they don’t have to pay those sky-high prison long-distance rates. And they’re growing – fast.

SMITH: They’ve even ditched that old prison name, Picturegram. The company has something that feels a little bit more 2015 – Pigeonly.

HENN: Like carrier pigeon.

SMITH: Like carrier pigeons.

HUTSON: I travel a lot, so I like traveling. And no matter where I go, even when I was in Japan most recently, there’s pigeons there. No matter where I go, there’s pigeons. And I notice how pigeons are so common that we never pay attention to them, even though they’re all around us all the time. And that’s kind of how I see our market a lot of times – is that it’s this market that’s here, and it’s present, but nobody’s really paying attention to them.


SMITH: That story originally aired in 2015, and Pigeonly is still in business. They still offer their picture services, but you can also send letters, articles and even money to people in prison. The company eventually raised $5 million in investment. After the break, our professor teaches us the fundamental lesson of entrepreneurship – figuring out what your customers really need.


SMITH: Hey, everyone. Class is back in session. And we’re rejoined by Columbia Business School professor Angela Lee, to whom I will turn over the laser pointer and PowerPoint slides.

LEE: Thank you so much for having me.

SMITH: I love the story of Frederick Hutson because, you know, it’s – he takes what, in many cases, would be a disadvantage, and he uses it essentially as his pitch for his business.

LEE: Yeah, talk about glass half-full and really seeing an opportunity.

SMITH: I feel like everyone looks around constantly and says, oh, I have an idea for this business. I have an idea for this business. What’s the difference between some idea you have that would be great in the world and an idea that is an actual, workable business?

LEE: I do think that there is this myth of the visionary founder sitting in a room. And then they’re just walking along, and the genius idea hits them…


LEE: …Across the head. And I really, really disagree with that myth.

SMITH: Really?

LEE: Yeah. We say that we invest in data-driven learners, which is just so not sexy, right? People want to be a visionary, a maverick. But at the end of the day, I think that really great entrepreneurs are ones who run a lot of experiments. They look at the data, and then they respond according to that data.

SMITH: Well, when we played the story of Frederick Hutson, he’s inspiring. Is he also a data-driven leader?

LEE: Absolutely. He knew what the typical response rate was for direct mail, and he knew that his was way higher. And he was trying different customer acquisition channels – different ways to get customers to talk to him – and figured, oh, this is the one that works.

SMITH: OK, let’s go over the very first thing you need to do if you have this vague idea and you want to turn it into a business.

LEE: The first question as investors we ask founders is, tell me about who your customer is. And we’re typically looking for three things. The first thing is demographics. The second thing is psychographics, and the third thing is problem. In terms of demographics, these are things like age, gender, income, education level. Most founders know this pretty well. The second thing is psychographics. Psychographics is – can I picture this customer in my head? What are they wearing? Where do they go shopping? What magazines do they read?

SMITH: In the case of Frederick Hutson, he lived with them, or it was his own family.

LEE: Absolutely.

SMITH: Yeah.

LEE: And then the third thing is, what is the problem you are solving for this customer? And I find that people often describe problems and products as, like, here are the 17 bullet points of why my product is great. And what I always say is, that’s great. I love that you have 17 benefits and features, but I’m one human talking to another human. And I say, you have to try this app, this product. What do I say to my friend? And if you can’t encapsulate it in a human voice in a few words, to me, you don’t really understand the problem you’re solving for your customers.

SMITH: In fancy business schools, they call this the unique value proposition…

LEE: Yes.

SMITH: …which is a fancy way of saying what?

LEE: Do you understand the pain point you’re solving for your customer?

SMITH: Pain point being the thing that drives them nuts – that they would pay money to solve. So in the case of Pigeonly, the pain points for prisoners were how hard it is to get a picture of your mom or your girlfriend and how much they had to pay for simple services that we all take for granted, like using the telephone.

LEE: Exactly.

SMITH: So if I am thinking about starting my own business, what can I learn from Frederick Hutson?

LEE: The two things I think you can really take away from Frederick’s story is, one, talk to your customers. I think a mistake a lot of founders make is say – that whole, like, I’m going to sit in my garage for two years and build something brilliant and then unleash it upon the world is just very silly.

SMITH: And never ask anyone, would you actually pay for this thing?

LEE: Exactly. So what I love is that he started talking to customers really early – while he was in prison, but also once he left as well and he was at the halfway house. So talk to your customers. That’s one big message. And the second is test your idea. Don’t think that you are going to be brilliant and unleash something upon the world. Test it by maybe doing a survey, maybe creating a really simple email newsletter to see how many people open or click on the shiny green button. Testing is key.

SMITH: And be willing to pivot – to change what you’re doing in response to what you actually hear and what people actually want.

LEE: Absolutely. I think being flexible is very much the name of the game.

SMITH: OK, let’s do a quick recap here. Know your customers. Figure out what’s causing them pain and how you alone can solve it. And start to test your solution. Actually listen to what your customers are saying. Then, and only then, can you start to think about the money. That brings us to our second case study about how to find the money to start a business and how to figure out how much customers are really willing to pay. It’s about a pair of twins who saw a delicious pain point but then weren’t quite sure about the next step. Producer Brittany Cronin has our story. It aired on The Indicator in 2021.


BRITTANY CRONIN: RaeShawn and LaShone Middleton are both trained chefs. But at the beginning of the pandemic, they lost their restaurant jobs. And as the months went by and they waited and waited for restaurants to reopen, they started to get worried. What if their jobs just never came back?

LASHONE MIDDLETON: All we know is restaurant. So it was one of those things – it was whether or not – are we going to go back to restaurants and not be guaranteed a job? So we were like, we have to figure something out.

CRONIN: And then one day, they get this idea. They’re hungry. They decide what they really want are some steamed crabs. But it’s late summer, it’s pouring rain outside, and they don’t want to leave home to go get the crabs.

L MIDDLETON: Literally, I was being lazy and didn’t want to go get the crabs and realized no one delivered steamed blue crab.

CRONIN: So RaeShawn and LaShone are like, wait a minute. We are trained chefs, and we’ve grown up on crabs. They knew some people in the crab business and decided they could buy and steam and deliver crabs by themselves. They had a car. They could cook in their mom’s kitchen. So they made up some advertising flyers – steamed crab delivered to your home.

L MIDDLETON: I had woke up, and I was like, OK…

RAESHAWN MIDDLETON: I’m going back out – yeah.

L MIDDLETON: I’m going to put the flyers up. But I was, like, shaking. I was, like, so nervous ’cause I was like, this is ridiculous. Like, how am I going to – I’m not going to start a business. Like, it’s one of those, like, moments where you’re like, am I really going to do this?

CRONIN: So they go out. They’re putting up flyers. They have low expectations. This is just Day 1. And they are pretty immediately confronted with the one thing that they had not yet done.

L MIDDLETON: The last door was my neighbor, and she was like, OK, put me down for a dozen. I was like, are you serious? Mind you, we didn’t even have prices yet.

R MIDDLETON: Yeah, we didn’t have prices.

L MIDDLETON: We didn’t what we were doing.

R MIDDLETON: We didn’t think anyone was going to order right away. We didn’t have prices. We – she…

CRONIN: Oh, my gosh.

R MIDDLETON: …Was like, how much? We were like, uhh (ph).

L MIDDLETON: I was like, I don’t know – like, $30.

R MIDDLETON: So we just made up a number.

CRONIN: A dozen steamed crabs for 30 bucks.

L MIDDLETON: And to put that into perspective for you, most places sell extra-large crabs…

R MIDDLETON: Extra-large meals.

L MIDDLETON: …For a hundred dollars. We sold it for $30. And – because we…

R MIDDLETON: Not knowing ’cause we just didn’t do any research. We were just like, let’s just try it. And so then when people start biting, you’re like, wait. Really? This is actually working? Oh, wait. Wait. We actually got to – we actually have to get it together.


SMITH: That story from Brittany Cronin in 2021. When we last spoke to the sisters a couple of years ago, they had raised their prices, and they were doing OK. They had about 10 to 20 orders a week. One sister would steam the crabs in their mother’s kitchen, and the other would deliver the orders. A lot of businesses started during the pandemic did not survive. The sisters even got offered their old restaurant jobs back. But RaeShawn and LaShone said no. When I called them last month for an update, they said, why don’t you come down and see our brand new restaurant, R&L Crab? We’ll visit after the break.


SMITH: RaeShawn and LaShone Middleton clearly had something their customers needed – fresh, hot crabs delivered to their doorstep. But ramping up a small family business to a successful brick-and-mortar store with employees – that took some figuring out.

R MIDDLETON: My name is Rae. It’s a pleasure to meet you.

SMITH: Good to meet you.



L MIDDLETON: Nice to meet you.

SMITH: When I arrive at R&L Crab, the twins are mopping the floor.

R MIDDLETON: I’m trying to prevent it from getting – it being super wet.

SMITH: I love that you’re doing your own janitorial work.

L MIDDLETON: Oh, we do everything here. We do everything (laughter).

SMITH: The restaurant is tucked into the corner of a strip mall. They now run the crab delivery service out of here, plus take walk-in customers. It’s been a wild two years. After our story on them aired, a TV network showed up to profile the sisters. They were running the business out of their mom’s kitchen at the time, and the crab orders started to pour in.

L MIDDLETON: We were just running out of space because once you go from 20 orders for the whole week, then 30 orders for just a day – once you go from that, now we have to hold onto way more crabs.

SMITH: Did your mom say you have to get out?

L MIDDLETON: She was getting a little fed up with the crab smell, I guess.

R MIDDLETON: Yeah, yes, for sure.

SMITH: I was going to say…



SMITH: …30 crabs a day…


SMITH: …Could probably smell up the place.


R MIDDLETON: She – it was getting a little hectic. It was.

SMITH: There is a standard playbook for expanding a successful business. Get a loan or investors. Hire people. Serve more of your customer base. But the twins told me they had no idea how to do any of this. They didn’t know who to trust. They made a crucial decision, though. Maybe they could get along by just reinvesting all their profits back into the business. They moved out of their mom’s place to a professional kitchen, hired drivers. But the money – the money was always tight.

L MIDDLETON: We were like, how are we going to pay for this? We have no money. We tried every avenue – banks…

R MIDDLETON: We both took out two personal loans.

L MIDDLETON: Me and Rae took out two personal loans separately to pay for it.

SMITH: Feeling a little overwhelmed, they brought on a business partner – an older man who was a friend and a mentor to them. They gave him a percentage of the business and hoped he would help them launch this actual brick-and-mortar restaurant. But then they all started to clash.

L MIDDLETON: All I’m going to say is that I think there was a moment where he forgot that we were the CEOs and the owners, and it started to be more his business and not our business. It started to be like, I own the business. You can’t tell me anything. This is my store, my business, completely forgetting R&L.

SMITH: Lawyers got involved, and the twins learned an important lesson. Be careful going into business with friends and family. The twins say the partnership has been dissolved, but they did manage to get the restaurant open.


SMITH: They give me a short tour. There’s a large kitchen, plastic bins in the back for the live crabs.

L MIDDLETON: Today we got – what? – 13 boxes dropped today.

SMITH: Thirteen boxes of crabs?

L MIDDLETON: Thirteen boxes, yep.

SMITH: They’re a gorgeous, bright blue.


SMITH: I didn’t expect that.

L MIDDLETON: These are Louisianas.

SMITH: There’s an order up for a half-dozen, and the little guys do put up a fight.


SMITH: Giant pot, of course – and then you just throw them right in? And, now, you have a secret ingredient.

L MIDDLETON: Yes. We use beer.


SMITH: What kind of beer?

L MIDDLETON: Ooh, we can’t say.


L MIDDLETON: We can’t say.

R MIDDLETON: We normally don’t tell.


L MIDDLETON: We don’t tell anybody what beer we use.



SMITH: LaShone and RaeShawn say they don’t want to go back to working for someone else. Even though they are in debt and always hustling for new customers, they say their happiest times are when they’re working holidays, knocking out 60 orders of crabs and dancing along to the music in the kitchen.

R MIDDLETON: For us, it’s worth it just because we’re – I feel like we were born to be entrepreneurs. You get more of a quality of life, so you just got to choose your balances.


SMITH: You say more quality of life. But when I walked in, you were mopping the floor.

R MIDDLETON: It’s not – to me, that’s not work. To me, that’s just taking care of my store because I love it. Like, I’m so grateful, you know? Like, opening the store was a huge moment and accomplishment. And then sometimes, you just remind yourself sometimes, even if you’re cleaning and you’re wiping down something, you’re reminding, like, I started – I was in my mom’s house. I was in the ghost kitchen. Now I have a store with my name on it.


TIFFANY EVANS: (Singing) Could a girl say no?

SMITH: That name again – R&L Crab in Columbia, Md. Stop by and say hi.


EVANS: (Singing) It was your heart he felt. Now it shows.

SMITH: I’m going to bring in our professor again, Angela Lee. What’s a big lesson you can learn from the crab story from the crab twins?

LEE: I think a big lesson that everybody should be aware of is that entrepreneurship is really hard.

SMITH: Yeah.

LEE: I hear a lot of folks say, I’m going to quit my day job and I’m going to go open a bakery. Or I’m going to go open an ice cream shop. And there’s this very idyllic view. And I think just recognizing that you’re going to be doing everything, especially the first couple of years – and I always tell people to talk to an entrepreneur. It’s not this dream-like state that you might think it might be.

SMITH: And for a lot of small businesses, it’s not like venture capitalists are beating a path to their doorway. The businesses are doing something called bootstrapping. So what is bootstrapping?

LEE: Yeah, so when you’re starting a company, you need money, right? And there are two ways to get that money. One is from customer revenue. So you sell crabs, you now have money to invest and maybe buy a second car or to buy a larger kitchen. The second way is to raise outside capital from venture capitalists who will just say, here’s a couple hundred thousand dollars or $1 million. They are going to get something in exchange for that money. And what they get in exchange is a percentage of your company. So the benefit of bootstrapping is you own 100% of your company. And you have control over exactly how you run it, how fast you want to grow, where you want to expand geographically. The drawback is you have to make money to get money.

SMITH: (Laughter).

LEE: And so it’s a little bit of a slower growth process.

SMITH: Or have credit cards…

LEE: Exactly.

SMITH: And someone willing to give you a personal loan.

LEE: And then on the venture capital side, the benefit is, typically, you’re going to get faster injections of capital. But the drawback is somebody now owns 20, 40, maybe 60% of your company.

SMITH: How can you decide which route to go? It seems like taking a lot of money from people is the more fun route, but maybe not.

LEE: You know, it’s funny. When people ask me this question, they expect me to whip out an Excel spreadsheet or to start talking numbers. And the first question I ask them is, what do you want your life to look like for the next five to 10 years? Do you want to take vacation?

SMITH: (Laughter).

LEE: How many hours a week do you want to work? And if the answer is you want a reasonable lifestyle, you probably shouldn’t take venture capitalist capital. They are going to ask you to grow very quickly and work very hard for probably the next five to 10 years.

SMITH: Angela, you’re scaring me here. You’re saying it’s hard to be an entrepreneur, that you have to really understand your customers. And there are people who want to take advantage of you. You might go into personal debt. You teach venture capital. You teach people how to be better entrepreneurs. And yet it seems like you’re saying don’t do it. It’s terrible. It’s a lot of work.

LEE: I think my job as an educator is to explain the realities of this. And I do spend a lot of time saying, this is what your day is going to look like. This is what your week’s going to look like. This is what your year is going to look like. And I also think, for those of you who are listening and thinking about doing this, go talk to five founders who are in year three of their startup and literally ask them, you know, how are things going? What are you struggling with? And if you hear that and you get jazzed and get excited, then by all means go forth and conquer.

SMITH: Angela Lee is a professor at Columbia Business School. Thank you so much for joining us.

LEE: Thank you so much for having me.


SMITH: We will have seven more classes here before you can get your PLANET MONEY MBA. So tune in every Wednesday until Labor Day. And on our very last episode, we will have a treat. We will take your business idea pitches. If during this episode you thought of something cool that can solve a problem, you could try it out on our business school professors. It’s like “Shark Tank,” but no one will be mean to you or give you money – kind of a guppy tank. It doesn’t have to be some big invention. It can be just a tiny thing that you want changed in the world. When I was in business school, I pitched a portable campfire on a bicycle that you could then make s’mores wherever you wanted.

S’mores cycle did not take off, but your idea might. So send us an email – [email protected] – and put pitch in the subject line. We’ll even invite professor Angela Lee back to give you feedback on your plan. As you’re thinking about your pitch, remember these vocabulary words this week, demographics and psychographics. Who are your customers, and what are their lives like? And most importantly, what problem can you solve for them? This is often called a pain point. And your solution is your unique value proposition. One more term, bootstrapping – when you build your business, as you go along, no outside investment.

PLANET MONEY Summer School will be running every Wednesday until Labor Day to ease those intellectual pain points. Bring us along on your adventures. And remember; PLANET MONEY+ members get to enjoy sponsor-free listening for both Summer School and our normal episodes. This series is produced by Max Freedman. Our project manager is Julia Carney. This episode was edited by Jess Jiang and engineered by James Willetts. The show is fact-checked by Sierra Juarez. PLANET MONEY’s executive producer is Alex Goldmark. I’m Robert Smith. This is NPR. Thanks for listening.


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