Afford Anything - [E] The Myths We Believed About Startups [GREATEST HITS]

Episode Date: December 26, 2025

#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth. ____ In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then? Build a startup. Raise capital. Scale fast. Get rich. That was the dominant story. But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture. Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business. He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure. From there, we move into one of the most misunderstood ideas in entrepreneurship: the difference between service businesses and product businesses. Rand breaks down the trade-offs. Services generate income faster. Product businesses rely on outside capital. And founders often earn far less than people expect. That leads to a deeper conversation about incentives. Once venture capital enters the picture, priorities shift. Profits matter less. Growth matters more — and it affects both the business and your personal finances. High revenue does not automatically translate into personal wealth. We also talk about the side of entrepreneurship that rarely makes the highlight reels: Loneliness. Anxiety. Depression. And the relief that comes from realizing that even the most successful founders often feel lost while they’re building. This conversation feels less like startup advice and more like a long-term framework for thinking clearly about risk, money, and meaning. If you’ve ever questioned whether entrepreneurship automatically leads to financial freedom, this episode offers a grounded and very honest answer. Timestamps Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Facing creditors and repayment negotiations (08:50) How a services business really works (11:40) From consulting to software (15:00) Services vs. product businesses (12:20) Why high revenue doesn’t mean personal wealth (25:05) Venture capital incentives (27:50) Founder salaries and financial reality (30:40) Startup mythology vs. lived experience (33:20) Loneliness and mental health (36:15) Founder strengths and weaknesses (39:50) Feedback and self-awareness (42:30) Designing a business that fits your life Learn more about your ad choices. Visit podcastchoices.com/adchoices

Merry Christmas, Happy Holidays. Today is Friday, December 26, boxing day to all those who celebrate. Today we are airing episode five of five in our special five-part series on F-I-I-R-E. So every day this week, we have aired an episode from The Greatest Hits Vault. What does that mean? It means we reached into the archives to find some of our favorite episodes, our greatest hits. around the theme of F-W-I-R-E. So on Monday, we did the letter F, financial psychology.

On Tuesday, we aired an episode around the first letter I, increasing your income. Wednesday was the second letter I investing. Thursday was the letter R, real estate. And today, we are sharing with you the letter E entrepreneurship by replaying this interview. This originally aired in September 2018. and it's an interview with an incredibly impressive entrepreneur named Rand Fishkin. Rand is a college dropout who spent his early 20s spiraling into a lot of debt. He tried to grow a marketing company, but he funded it in the worst possible way.

He leased expensive office space. He hired very expensive contractors. He rented booths at conferences, and he paid for everything with a series of credit cards. He ballooned his debt up to $150,000, and then he couldn't make the minimum payments and defaulted. And with late fees and penalties, his debt swelled to over $500,000, $500,000 in credit card debt. And no, he did not declare bankruptcy. He stayed the course. He doubled down at work.

He negotiated with his creditors. And dollar by dollar, he pulled himself out of debt and grew his company in the into a business that at the time of the interview was doing $30 million a year in annual top line gross revenue. How did he do that and what lessons can we learn? We're going to discover that in today's episode. Enjoy. Hey, Rand.

Hi, Paula. Thank you for coming on the show. I want to just dive right in to how you got started. You are now what most people would consider to be very successful. but a younger Rand had half a million dollars in debt. I'm giving away the problem here, but can you describe exactly how you got into that situation? Yeah, it turns out when you stop making the minimum payments on your credit cards because you can't afford to, the interest rates and penalties rack up pretty darn fast.

And that's what happened to my mom and I. We started a web design, web marketing business back in, well, in 2001, I dropped out of school to join her firm and basically do that with her. And it was just the two of us for a long time. And we made every mistake in the book. You know, we spent money on all the wrong things. We hired people that didn't work out. Use subcontractors that didn't work out. We accepted contracts from clients who didn't pay. We thought we needed fancy office space to be able to close deals and signed a lease that we couldn't really afford. And once we had about 15, thousand dollars in debt. I think that was in 2004. We were unable to make some of the minimum

payments on that balance. And we were paying ourselves. I mean, my mom was taking home nothing or next to nothing. I was taking home $400 every two weeks. So, you know, not even enough to pay the rent. And I was living with Geraldine, who was my girlfriend at the time. She's now my wife. We ended up with this half a million dollars in debt and had to find a way to dig out of that over the next few years, which was pretty painful itself. So that $150,000 was, were your expenses and the remainder was interest and fees? Exactly. Wow. Ouch. And this was all on a personal credit card, correct? In your name? This is on about a half dozen different, mostly credit cards. One, I mean, one was like an equipment loan for our office equipment and computers and stuff. And I

think one was like a small business loan. But yes, maybe all in my name except for one that was in my mom's name. And how old were you at this time? I was 22 when I dropped out of school and started working there. So between the ages of 22 and 25. Wow. That's quite a way to start your life. It was jumping in the deep end for sure. And I think that it's not something that I recommend to folks who are now trying to build startups and build companies, especially in the tech in marketing world, which is where I am, you know, the advice I give is certainly, hey, spend some time at another company or two, even if it's sort of a painful, no fun experience, because even just six months at another job, I think, would have really opened my eyes to what the

working world is really like, as opposed to having to do everything for the first time. At the time that you had all of this debt, you had the experience of debt collectors showing up in person, which I'm not sure I've ever met anybody who has had that experience. Tell me about that. Tell us about that. Sure. I can tell you it is much worse than a postal worker showing up at your house and dropping off mail. But I've heard much better than a bounty hunter looking for you because you skipped bail. So right in between those two. Yeah, it's a weird experience. I mean, it definitely, it's one of those stomach dropping sort of scares you a lot, even though the consequence is not actually that significant, right? It's just an intimidation tactic that

financial agencies use to try and muscle you out of money. It is legal. It's certainly legal and reasonable as long as they're not overtly threatening violence or things that they can't actually threaten. But one of the big things that they will threaten you with is papers that say you're being sued for this amount and you'll have to go to court and all those kinds of things. And thank Hopefully, I did not end up having to go to court. My mom sort of managed the financial side of things and essentially made deals with these collections agencies and with the banks. And over, I guess that would have been over the next three years, we were able to pay off that debt. Not that we didn't end up paying the full 500,000, right? So my mom, Jillian, she would call up a bank, say, Bank of America, right? She'd say, hey, we owe you, you know, $100,000. But the original sum that we owed you was, $10,000, and this is $90,000 in fees. How about we pay you the $10,000 and you write off the rest? And basically, you know, my credit report looked terrible, but they didn't come after us for more money or try and sue us and send us to court. So it eventually worked out, but it was

a terrible, terrible way to go. And it's completely backwards because the way a services company, right, we're consultants, we're building people websites and we're doing the design and then we're helping them with the marketing and, you know, later years, SEO, search engine optimization, that should be an extremely low cost business, right? You can do it from anywhere. You don't have to have a big team or employees unless you have lots of clients. So, you know, we just made all the mistakes. And you never told your dad. He eventually found out, but you didn't tell him. Yeah, that's right. My dad's sort of an interesting guy, and he's got a lot of anger issues. And and a lot of issues around money in particular, and we both sort of thought that he would not

react well to that. And so, well, I think we worried it would be much more severe than that, right? I think my mom worried that, you know, would sort of break up to the family and that he would try and step in and make a worse mess of things, and that anger would be unhandleable, which I think based on experiences around, you know, for getting a coupon at home and seeing how he reacted to that, I can understand where she was coming from. Wow. So tell me about what happened next. As you said, you had a consulting company, a marketing consulting. How did you proceed from there? How did that lead to your next business? During this time period, I think it was actually 2003, we stopped being able to pay our subcontractor. in the SEO field, and we basically had promised that work to clients, and so I had to learn some of those practices, including SEO. And so basically, you know, did a lot of research in the

field and tried to figure it out. It was very complex and confusing and a very opaque industry and secretive. The search engines themselves, you know, Google and Microsoft and Yahoo were super secretive about how they operated. And so I created this website called SEO Maws, which tried to open source a lot of the information about how SEO works, at least everything I could figure out about it. And that was a mediocre blog back in the early 2000s.

And then over time, I got better at writing. And I got invited to speak at conferences because of the success of this blog. I think I learned sort of what worked in the industry. And I was able to have some success for our clients, which helped us to make some money. And then that also brought in new consulting clients.

And that's how we were basically able to pay off the debt. So we built this reasonably successful consulting practice over the sort of four years following the creation of that blog. And in 2007, we launched a software subscription. We didn't really know what it was. But we had some tools that we had built. We put up a little PayPal paywall. so that you could send us $39 bucks a month and get access to the tools we'd built to do SEO for ourselves and our own clients.

And in the middle of that year, we looked at the numbers and said, oh, my gosh, this software subscription is making as much as our consulting business. And it's only been around for six months. We should double down on this thing. And so at the end of that year, we had paid off the last of our debt, and we raised a round of funding from a venture capital firm here in this. Seattle area called Ignition Partners. I was made CEO at that point and for the next seven years was CEO of this company and grew it from a few hundred thousand dollars to a little over $30 million in annual revenue and then stepped down as CEO, worked there for another three and a half years or so and just left recently to do a new business. Wow. All right. There's a lot in that

story to unpack. But the first thing, the first comment comes to mind is I've rarely heard of a person being $150,000 in debt, well, more than that, but $150,000 in principle. And then deciding to essentially start a blog as a way of getting out of that. Sure, yeah. So I think maybe the right way to think about it is that those two events are somewhat disconnected. Okay. One thing that I certainly had in my early 20s was a lot of cognitive dissonance and compartmentalization. So I knew that in theory we had this money. I knew that these debt collectors were coming after me. And, you know, it all seemed like kind of a pain in the butt. But I didn't process how sort of dangerous and life affecting and negatively impacting it might be if we didn't dig

ourselves out. I sort of just relied on my mom to sort out the financial side because I was just responsible for the work. You know, I was supposed to do the client work and the designs and the SEO and that sort of stuff. So I just kind of buried myself in that. And this blog was a almost like a personal passion project that was related to work, but not directly. And then it started getting us business. And that felt fun and good. And so I kept focusing on that aspect of it. And we got lucky. You know, we got very lucky that we were in the search engine optimization field at an early time, when there wasn't a lot of resources out there. We were lucky that I sort of became a good writer about professional topics

and that very few other folks in the field were open about what they were learning. I was very lucky that Google decided to stay so secretive as it grew and that they were very non-transparent with information about how they worked because it forced people to go out on the web and look for other sources like what I built with Maws. Yeah, we got lucky with the tools and with that business. got lucky that these venture capitalists were interested in backing us. So just a lot of right place, right time digging out. And yeah, I think that we executed well on some of our opportunities and poorly on others. You know, the book talks about mostly mistakes that I made.

But we were not super savvy to say, hey, let's build a blog and do content marketing and then build a software business because of the high margins and relatively low investment costs. We weren't thinking nearly that sophisticated about this stuff. That is one thing that strikes me about your story is that in hindsight, a lot of the decisions make sense, but it seems as though probably a universal thread of most entrepreneurial journeys is testing things, seeing what sticks, and then moving in the direction of what's working. Yeah, I think that's right. I think a lot of the very sort of financially or entrepreneurially successful folks I know, they muddle through a lot more than you'd think. And I think that's actually a wonderful thing. I think it makes the journey feel less inaccessible.

It feels like, oh, wait, no, this is a possible thing, right? This is open to other people. I can muddle through too. Everyone else made mistakes. Everyone else messed this up. Everyone else had these, you know, really tough times and hard struggles. So I am not alone when I go through that. I think that's actually been a big, big lesson for me is learning how not alone I am when I

screw things up, you know, in really bad ways. That's right. You described there was a scene in your book in which you talked about during the early years being invited to some type of a meetup in Seattle in which you were surrounded by people in the industry that you, whose reputations you had known for a long time, people whom you had really looked up to, other entrepreneurs. And when you met them, you were struck by how incredibly vulnerable they all were. Yeah, that's absolutely right. Yeah. So it's a group of Seattle entrepreneurs, which I'm, I'm still part of that group and, you know, and I've joined others as well.

And I think that feeling of being not alone is really, really powerful. I actually urged Geraldine last year or two years ago to build an email list with a few of her writer friends so that they could sort of share their stories and lean back on each other and, you know, ask for help and have discussions on these topics because I think that that feeling of not being alone is just huge. Reality says the odds are stacked against us to think our U.S. men's national team can ever raise the world's biggest trophy. You're the first soccer team to beat them at football. Never. But here's the thing about us. Refusing to accept reality is kind of our thing.

Being unrealistic, that's not a flaw. It's a force. It's fuel. Because if you want to be great and make history, never chase reality. Join U.S. Soccer Insiders today. be part of the journey. One of the things you talk about to get a bit more into the entrepreneurial weeds of it is the difference between a service business and a product business.

SEO, MAUS and later MAUS, was both. Can you describe what the pros and cons of each are? Yeah, roughly speaking, a services business is one that has relatively high marginal costs, meaning for each new client that you serve, each new person that you're helping, you need to invest quite a bit, right? A very similar amount to the amount that you invested with the last client. Maybe you've gotten a little more efficient or your processes and practice have gotten a little better.

But generally speaking, person A who needs a plumber and person B who needs a plumber, you're going spend a lot similar amount of time working on their on their house a product business is the 10,000th bottle of, you know, whatever it is, um, nut-based milk that you sell at the grocery store is vastly easier to produce and to sell than the first one was. And so it scales considerably better. That being said, usually a product-based business requires a lot more upfronted investment, usually requires a bigger team. It requires more sales and marketing efforts. Oftentimes, the cost of customer acquisition is such that the payback period takes a lot longer, whereas the plumber basically makes money as soon as they provide the service to that one client.

So, yeah, there's a lot of differences along those. I think one of the problems that I see is this myopic view that we have had. I think that's starting to change, but especially in the technology, world, there's a very myopic view that you can only be one or the other. You cannot have both services and product. I think that's totally wrong. And I think there's a bunch of companies that have proven very nicely that you can do that and do it well. You know, big companies like Salesforce and HubSpot and then plenty of smaller companies as well. I also think that there's a misnomer that having a product-based business

is somehow more impressive or more worthy of notoriety just because that's what the press tends to cover. They are much more likely to cover product-based businesses than services ones. And that's mostly because product-based businesses need a lot more press because they need to scale their customer awareness

and branding to get the new customer development they need. And I think there's a myth, a terrible myth that I tried to spend a good amount of time in the book busting that you as a founder will always or almost always make more money as a founder of a product-based business than you will as a founder of a services-based business. And that, in fact, from most of the examples in my world, the reverse is true. And that's because services-based founders tend to own much more of their business than product-based founders, because product-based founders have to almost always raise external capital. And because, in general, services-based businesses,

you know, as a founder, you can pay yourself a considerable amount more. You can take out the profits. And in a product-based business, that's really true. That's right. The math that you outlined in that book was pretty eye-opening with regard to the reality that a person could found a business that does eight figures in revenue and still not actually have that much money personally. Yeah, yeah. I mean, people are always shocked when they're like, oh, you built Maas, and you know, it's going to do whatever it is, $50 million or more in revenue this year, and you own, you know, 20% of that business and you're sort of the chairman of the board. You were CEO for a long time and you're the founder. So you must, you must be rich, right? Like, you must have a lot of money. And don't get me wrong. Geraldine and I certainly have more wealth than I think the average. American by a good shot. I think we're in the top 20, 25%, but certainly not the top one or even the top 10. We don't have a million dollars. We have less than that. We have a mortgage on our house and we live in a lovely city, which is Seattle and it's expensive here, but it's not nearly

the level of wealth that I could probably name 20 friends of ours who run consulting businesses and have much, much more money. And they're sort of shocked, right? Because they go, but Rand, I've only been running my business for five years. And it only does, you know, $2 million a year in revenue. Your business is 25 times that I'm out. What's going on? And then you have to explain that, you know, once you raise capital,

you can't really pay yourself the profits. Profits aren't actually the goal. Growth is the goal. And so the idea is that you take the profits and reinvest them in the business. So I had a nice salary at Maus. And now I have a nice severance from the company, which I very much appreciate. and is helping me get started with my new business, but it's pretty different.

You actually disclosed your salary in the book was as $220,000. That's right, yeah. Yeah, which is amazing, you know, an amazing amount of money, right? That's nothing to complain about. And I want to be clear that I don't disclose this stuff to sort of rub it in people's faces or to say like, oh, look how much money I made, or to try and say that, you know, this is a paltry sum either. I don't want to discount how lucky I want to. was to have that salary at the end of my career there. But I also want to be very open and honest for

people who might be following in that path and thinking, ah, if I build a successful company like Rand did, I will become vastly wealthier than if I stick to a services business or if I go work at Amazon for five or six years, because that's not true. You know, a level three software engineer at Amazon is out-earning me by 50% plus. Exactly. That was my first thought when I read that that was your salary was I was shocked that it wasn't higher because 220 is on par with what the director of a nonprofit might make, with what an attorney might make, a higher paid engineer might make. I mean, it's a wonderful salary, right? It's multiples of what an average American takes home, but it is not what I think people imagine it to be. Exactly. When you're the founder of a

company that does 30 or 40 million in revenue or 50 million in revenue. You just imagine quite a bit more. Right, right. But as you outlined in the book, there is that difference between starting a company that relies on outside investors and brings in outside funding versus not. And that creates an impact certainly on growth, but also on how much you're taking home at the end of the day. Yeah. And I think this is not just a story for founders, right? This is also something really important to consider as an employee, I think it's an important thing to consider as an investor. I think it's probably pretty important to consider as a voter, just to think about how economic distribution works and where it goes and why it goes in those directions. Certainly anyone who's thinking

about, you know, becoming an entrepreneur, starting their own business, or joining an early stage business should be thinking very hard about these things, right? Especially if they have financial requirements in their life related to family obligations or personal goals or obligations, health issues, all that kind of stuff. You know, this is stuff that really impacts folks. And I think the mythology is really unhealthy. And so it helps to have these other stories and the statistical data to combat that. What do you hope are some of the major takeaways from the book? My biggest concern and the biggest reason that I wrote the book was I worried about how pervasive the Silicon Valley startup mindset was becoming in business overall,

right? I think that it's impacted how entrepreneurs in hundreds of sectors that have nothing to do with tech think about building a business and what gets amplified in the press and what popular culture covers and how entrepreneurs and small business owners think about what they're up two all the time. And so the biggest thing I wanted folks to do was to challenge some of that thinking, to ask whether those are the right things for them. Because not everything, certainly not everything that startup culture has produced is terrible. Some of it is really cool and awesome and can be wonderful when applied to your business and can be healthy. And then a lot of it is very specific to only that world and maybe not even right for our world. And so certainly

shouldn't be applied to other places. Most of Lost and Founder is challenging. those pervasive myths of, you know, how should we hire and fire people? How do we build culture? What actually does culture mean? Company culture mean? What are core values and why they matter? And when do they mean something? When do they not mean something? And then talking a lot about finances. And there's certainly a couple of chapters that touch on raising outside investment and what, you know, what you can expect if you do or don't. Spend some chapters talking about issues around depression and anxiety, which are pervasive in the entrepreneurial world, no matter what sector you're in. And then a lot of a combination of sort of personal

advice and professional stories that I think might lead people to another direction in their careers. Are there any specific examples of myths of startup culture, specific examples that you would want to name? Oh, sure. Every chapter in the book, actually starts with a quote from some notable Silicon Valley startup person, your Elon Musk's and your Peter Thiel's and these types of folks, Mark Andreessen. Right. One of them, Jason Freed is going to come on the show in a couple of weeks. Oh, awesome. Yeah, terrific. You can give them a hard time about that one. No, actually, I'm a huge of startup luminaries. Jason is definitely near the top of my list.

But yeah, a good one would be, I think it was Jason's quote, was the one. that's related to, you know, building product is the easy part, right? Building software, that's the easy part. It's acquiring customers and doing the marketing. That's what's difficult. And I challenge that very directly. I think that is true for you because you come into, you know, you Jason, right, come into the startup game with these particular skills.

And I think it pays for an entrepreneur to be very self-aware and to invest in self-examination to understand why, you know, something that is hard for them might be easy for other people and what's going to be hard for them and whether they can build a business that plays to their strengths and that not just compensates, but almost avoids their weaknesses. For example, I hate doing sales. I dislike it. I think it creates a lot of inauthentic behavior and I don't like the relationships that get formed from sales communications and I never wanted to build sales team. I have a few friends who are in the sales world, but I tend not to like salespeople. And so I built

a company that was completely self-service and required no salespeople, as opposed to, oh, how do I find a co-founder who's good at that? Or how do I get good at that over time? I just said, I'm not going to do it. It's those types of lessons of, oh, it's not just this one path that's an option. Here's another path that's an option. And you made the point that a founder's strengths and weaknesses will be inherited by the rest of the company, almost passed down in the genetic code. Yeah, that's exactly right. And as a result, that's why it's so important to understand what those strengths and weaknesses are so that you remain aware of it as it grows throughout your company, right?

And as your company scales, those missing elements and those strengths become magnified. So how do you, and I realize this is actually a much broader question, but how do you develop self-awareness? Yeah, I think you have to make it a discipline like anything else, right? So one of the ways of doing this, and I talk about a few in that particular chapter, but one of the ways of doing this is to keep a log of successful projects, successful hiring, confidence that you have about interviewing people, confidence that you have in your network, and you will often be able to identify those things.

then it's consistently your job to revisit that and to look at, hey, I once was great at marketing. Now, four years later, it looks like because I've taken my eye off of that or because the field has advanced or whatever it is, it looks like that's becoming a weakness that I need to reinvest in or that we, as a company, need to reinvest in. So I think that's an ongoing practice, not a one-time thing. Right, because there will always be unknown unknowns. Yeah, you can spend your whole life getting to know yourself. I actually think that's one of life's great adventures. How important is feedback from others? And what I mean by that is how do you discern between what is helpful and what is noise? This is one of those things that I think was always tough. It is helpful and I think wise for relationships to not keep score.

right so you know you and your romantic partner you and your business partner you and your employee right you don't keep score about who was right and who was wrong and how many times and therefore we should not listen to you anymore and we should only listen to me that kind of thing and i totally get that instinct but it's also helpful to have some sense of it so that you can wait feedback and wait the opinions of other folks right there are there are people who develop expertise or have skills and you should in a particular arena or broadly and their opinion or the opinions of several people like them should carry more weight than people who are not very familiar with those fields don't have that expertise those kinds of things so i think

that that's one challenge in that another one is that we found that anonymous feedback internally externally, obviously it has a bunch of challenges because of astroturfing and sort of the nature of the web. But internally, we found that anonymous feedback was often inaccurate,

overweighted to negativity and sort of personal grudges, whereas transparent feedback where folks identified as themselves was much healthier. So I would definitely urge people to go that route if you're looking to get feedback

from your team. I also think that one-on-one conversations are a much better way to get more real feedback, but you have to first create an environment where people don't feel like their jobs or livelihood or reputations or career progression are threatened by the feedback that they give. And the only way to do that is to call out people who've given very critical feedback in positive ways and to recognize and reward them in front of the whole team. and that's a hard thing to do. A lot of people don't have the, I don't know, they're too arrogant or too conceited. They don't feel like they can be vulnerable in that way.

It's a hard thing. What are some other ways to create transparency and to create honesty within a team? I think that it depends on... So first off, I want to be clear that, you know, in the book I talk a lot about transparency because it's very important to me. However, I don't believe that transparency is a,

a panacea or that everyone should invest in it. I think you should only invest in it. And if it is a core value for you as well. So I use transparency as an example of a core value, but I'm not suggesting everyone take exactly my core values, right? You should have your own. That's what should be part of your company. Building your own is a much better idea than using someone else's because you think they'll help get you ahead in business. If your only goal is to grow your revenue or your profitability or whatever, then, okay, fine, you're Goldman Sachs, right? That's your, you know, your true north is just money. And I think it can actually pay to be transparent about what your values are so that you attract the right kind of people. And that can work well. But in terms

of building it, if you decide transparency is a core value, it's something we do want to invest in. I think you have to recognize that transparency is very different than honesty. honesty is just saying things that are true. Transparency is identifying things that are uncomfortable that people would not normally share, that create a pit in your stomach when you think about telling other people about them and then choosing to do that anyway. And that's incredibly difficult to do, particularly publicly. For a lot of people, it really is. How did you have the courage to continue growing to kind of contextualize that? question a little bit. Thinking back to your very early days before you received any outside funding,

you described yourself and there was one other guy, I think his name was Matt. Yeah, yeah, Matt didn't mention. Yeah, and you were both taking home, what, $1,600 per month? You guys were both taking home so little at the time. My mom was taking home nothing. And your mom was taking home nothing. And it would have been so easy to stay where you were. And as you grew, as your company got more profitable, not added more team members, not made more investments, and just focused on earning, kind of eating the profits rather than investing in growth. What gave you the courage to grow and how did you figure out how to make wise decisions between what to take out and what to put back in? So I might challenge some of the phrasing of the question

because here's a good example, right? I left Maas at the end of February. I started a new company, Spark Toro. We raised some money at very favorable terms. And my co-founder and I are planning to build a very small, very profitable company. So intentionally doing exactly what you said, right? So I'm not sure that it was courage. I think, in fact, that it was a feeling of not being worthy and not being good enough, a feeling that to be taken seriously as an entrepreneur, to be respected, to earn the attention and praise that I wanted. We had to grow big. We had to be like the big kids in Silicon Valley and raise a bunch of money and build a big team and have a lot of revenue. And whether we made money was not the focus of that. And whether we were happy

was not the focus of that. And whether we were, you know, bringing something wonderful to the world was not the focus of that. The goal was a high growth rate and a lot of revenue and people, right? Because those were the things that I thought were impressive. Those were the things I thought would sort of, I don't know, make me look like all the other people who were on the covers of magazines and getting written up in TechCrunch and were admired by their peers. And I think that's still true today. I think that a lot of people biased to doing the thing that seems like it will get them sort of looking like the people they admire rather than questioning why they admire them and whether that's a life that's good for them and pursuing those kinds of things. So I want to be clear.

I'm glad that I did it because I think if I hadn't raised venture capital, if I hadn't built a big or a medium-sized company and pursued growth and gotten to a size I was uncomfortable with, I think I would always be questioning myself. I would always be saying, boy, Rand, you are just, you're not good enough. You have high potential, but you're a low achiever. I think that's what my data was said about me. And so I think as you get older and you experience these things, you go through them, then you come to the realization, the awareness of, hang on a minute, that's not really what I want. I don't want the thing that the magazines are selling me. I want this other thing. I want to build a profitable company. I want it to be small in number of people who work there.

Small might mean 10. It might mean 50. Could even mean 100 someday. I'm not putting that, but it doesn't mean a thousand. And I don't want the constraints of being forced to grow and not being the only path to success and to an exit. So yeah, I think this is a sort of lesson that you learn over time. So yeah, the thing that encouraged me to do all those things with Maas was not, I don't think it was courage, at least not in the classic sense. I think it was. jealousy or gosh, you know, a feeling of not being worthy, of not being good enough, of needing to prove myself, I think those are the drivers. Were you aware of that at the time? No, God, no. Just, you know, a 20-something kid doing this thing that he thinks is impressive and not really having the realization of, wait, maybe I'm doing this because I've been sold a sort of late-stage capitalism bill of goods.

Tell us about your new company, SparkToro. Sure. Yeah. So it is also planning to be in the marketing software world, but not in not an SEO specifically. So we hope to basically build a large database that people can search of all of the sources of influence across the web and hopefully some offline as well so that you could rather than spending weeks or months of work and or paying a PR firm tens of thousands of dollars, you could in just a few minutes, you know, say, what are the publications and people and sources of influence that architects or foodies or mid-century modern furniture enthusiasts or plumbers, what do they pay attention to and how can I best reach them? One of the missions there is definitely to help marketers to do a better job with that and get more accurate, more complete data in a fast way. And also to sort of disrupt a little bit of the duopoly of marketing spend that is currently dominated by Facebook and Google. I think that there's a lot of, a lot more opportunities for people to do marketing,

but the default is just, well, let's buy some Facebook and Google ads and we'll call it good. Exactly. Yeah, that's always the first thought, right? Buy some targeted ads aimed at people who like X page. Yeah, exactly. Right. And how awesome would it be if you could also go to a, hey, for audience X that I want to reach, where else are they? Oh, they subscribe to this subreddit. Oh, they listen to these three podcasts. Oh, they go to this event. Oh, they read this blog. Hey, I could go do some marketing in all of those places, organic or paid marketing, right? I could try and be a guest on this podcast. I could sponsor this event. I could see if I could be a speaker at that event. I could write a guest post for this blog. I could sponsor this

blog. And I think that most of those opportunities get ignored because potential advertisers and brands don't even know that their audience exists in those places. I can see that being a benefit in really for both segments because then the producers of those podcasts, the writers of those blogs, then get more attention from people who want to work with them. This is definitely a, I hope to help the marketers. I also very much hope to help the publications. You mentioned speaking at conferences. I've always wanted to ask you this because I've heard of your travel schedule for a very long time. I know you travel a lot.

How on earth are you productive while traveling? I am definitely less productive while traveling. The only way I really justify and make up for that is that my experience has been that in-person relationship building, getting on a stage, it's so much different than someone who read a blog post or someone who saw me on Twitter. I say me, but the brand, whatever, Maas, or SparkToro, or whatever it is that I'm doing, the value is tenfold increase. And so if it means that for a week, my usual productivity is at 50% or 40% of its usual load, that's okay. It's a worthwhile tradeback.

It surprises me to hear the SEO guy say that. I know, right? But it's absolutely true. So the closest thing to it is video, which is why Whiteboard Friday, the video series that I did at Maas, was so usually important because people watching you on video and sort of consuming you on a regular basis, consuming your content on a regular basis in a video format with a human being that can connect with, much more powerful. And then shaking a hand, seeing someone on a stage, even more powerful than that. What has surprised you the most throughout this journey of going from from being half a million in debt to being in this place where you are now? I think perhaps most surprising is the discovery of why so many things that I believed just a few years ago or early in my career or I'm sure things that I believe now, how over time new ones, and experience and reflection and purposeful work can combine to make those untrue over time or to make them seem much more complicated than they were originally. You know, I think that the, I don't know, whatever it is, right, that we're just wired to want simple answers to things, black and white. This is better than that. Product is better than

services revenue. You know, raising money is better than not raising money. And the answer is never it's never completely the other way. It's always, well, this is a bunch of shades of gray. Here are the shades of gray. Here's what's maybe right for me and maybe right for somebody else. I think that nuance, that's potentially the most surprising thing, especially from my years and my early 20s when you're absolutely convinced that the world is one way and everybody else is not seeing it. So you've learned that the world is more nuanced than you had originally thought? Yeah. And I think that might be so broad as to not be valuable, right? But the, each of the beliefs that I hold can turn from,

I believe this 100% to this is a very nuanced and complicated thing once you expend time and energy digging into it. Have you found that the more you dig into something, the more nuanced it becomes? Or kind of the more you know, the more you discover how much you don't know? Yeah, I think that's exactly right. There's sort of that curve of expertise, right? Whereas as you grow your expertise, you know, in the early stages, you know nothing, then you feel like you know everything, and finally you come to learn that you know nothing. And then you have the confidence of knowing that you know nothing and that that is still vastly more than many other people, right? Which is something of a paradox, but also a really healthy and true thing. Absolutely. I see that in finance and I'm sure that that is true in almost every other arena as well.

totally yeah thank you so much for spending this time with us where can people find you if they would like to know more about you sure so i'm rand at sparktoro.com our website is sparktoro you can also follow me on twitter that's where i'm most active at randfish thank you so much randt and thanks to all of you for being part of the Anything community. Merry Christmas. Happy Hanukkah. Happy holidays. I hope you have enjoyed this five-day series in which every day Monday through Friday we have played an episode from the greatest hits ball around F-I-I-R-E. Financial Psychology, increasing your income, investing, real estate, and entrepreneurship. I hope you have learned a lot. Tell us which episode did you

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