067: Tiny Business, Big Money with Elaine Pofeldt
8 Dec 2025 · 37 min
Elaine Pofeldt talks about building a one-person business to six figures through systems, automation, and premium pricing. She uses U.S. Census data to show which micro businesses actually scale, and argues the goal is lifestyle first: flexibility and joy, not growth for its own sake.
Chapters
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Sometimes you do things manually, so to speak, that have other purposes. You don't have to take everything out of your life that you do that someone else could do. It kind of forces you to think about are you getting something out of how you're spending your time? If you're doing something that you hate, it doesn't involve anything that enriches your life in any way, then don't do it. That's the stuff you want to offload.
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Hello friends. I am so excited to be here today with Elaine Poffelt. Elaine is an independent journalist specializing in entrepreneurship. Her previous book, the million dollar one person business looked at how entrepreneurs scale to $1 million in revenue prior to hiring employees. I have to say I had her on the Pivot podcast episode 96 and it was one of the top 10 favorites of all time on that show. Today we're talking about her brand new book, Tiny Business, Big Strategies for Creating a High Revenue Micro Business. Elaine's work has appeared on CNBC and in Fortune, Money, Forbes, many other places. She lives in New Jersey with her husband and four children, which we talked about in a previous conversation that I'll link to in the show notes. Elaine, welcome to the show.
Thank you so much Jenny. It's so great to be back.
I am thrilled to have you and you and I share this moniker and love of studying tiny businesses. Tell us, how did you go from the million dollar one person business? What gave you the sparks of an idea to study what are sometimes called high propensity businesses where there is more than just one person involved?
One thing I noticed Jenny, when keeping in touch with the million Dollar one person businesses is that they're not static And a lot of them were transitioning to the stage where they were hiring their first employee or creating a more formal team. Since I had first interviewed them, one of the pain points many of them had was they were great at the independent life where they had a very loose team, maybe like a bookkeeper and an accountant, but they weren't really having to convey what they wanted done to other people. And they were struggling with this a little bit, transitioning to being a leader of a team. They wanted to hold onto their free lifestyle, but they also realized they could become a bottleneck if they didn't master this aspect of running a business. And so I started asking entrepreneurs I interviewed who had transitioned to that stage where they had maybe employees one to three or four. They now had 10 contractors and they had a Monday meeting or something like that. What were they doing to manage it and still being able to hold on to their free time.
Yeah, I find this category so interesting because you talk about early in the book that a lot of them do seek control and lifestyle. There are other entrepreneurs who stay open to the possibility that the natural sides of the business will reveal itself, and they're perhaps a little more open to growing it over time. But there is this segment of folks you even mentioned, Dana Derricks in the book, who really do want to stay small and yet earn big money. So this idea of the tiny business, big money, in Dana's story, he expanded to seven figure revenue and seven employees. But he later found it stressful to manage traditional employees and revised his business model to make it contractor based. So now at the time that you interviewed him, he had four contractors. What was your experience in talking with these business owners of who was happy to keep growing to sometimes 10 employees versus those like Dana who actually go, wait a second, I don't want that. Even if they don't want to work solo, they realize they don't really want that kind of overhead.
I think the entrepreneurs who are happier having the employees are the folks who commit to scaling in the traditional way. They realize what they want personally is something much bigger than a boutique business. And the only way to really scale it, unless you're a master of automation, is to have people on payroll because you need them there consistently. The folks like Dana really love their lifestyle. In addition to being copywriting genius, he's also a goat farmer. He has a small farm in Wisconsin and really loves that lifestyle. And he just found it added a lot of complexity to his life to have employees. And there is some complexity that comes with it. There's compliance, you've got to run payroll, you've got to run an organized business in a very traditional sense to meet the requirements of the government. And some people find that that's just too much to deal with and they don't want to. And they prefer maybe having a team of contractors around the world who help them, but it's a lot looser.
Yeah, that makes sense. You talked too about these teams that even if there are no full time employees, there is a cadence to the company. So whether someone's working with contractors or full time employees, there is a sense that these tiny businesses with big money have systems, they have process, they have automation, they do have outsourcing, but they also have a regular cadence. And it's a group of people working together toward the larger mission.
Definitely. And there's a chapter in the book where I looked at exactly how they're doing that because that was the area where people seem to have the greatest curiosity. And what was very interesting was some took a very traditional route where they have a zoom meeting or maybe they're even under one roof at a certain time and it's a traditional meeting, like a stand up meeting. And then others use very unconventional ways of managing the team. One person who I thought had an interesting approach was Brian Dean who has a company called Backlinko which just sold actually it's involved in SEO and Brian uses a tool called Notion to manage his team or just does one on one emails. He hates meetings and he doesn't have them at all. And I love that idea that you could grow a real team but use all digital communication. If you're just a person who hates meetings. I happen to be somebody who does not like meetings and so I thought that's really encouraging that you can just avoid them altogether.
Absolutely. I am obsessed with Notion. I also power my entire business with Notion.
Oh you do? Oh wow.
And in fact, listeners, you could check out the new Free Time toolkit if you go to itsfreetime.com toolkit that goes with the book and that I created in Notion. So for anyone who's Notion curious, it's a good way to see what it can do. But yeah, I moved my whole operation over to Notion. And I'm similar. I don't love meetings. I mean, in the past I used to have one on ones with each team member once a month and I had a team all hands once a month. And I knew other entrepreneurs were doing these weekly, but I just couldn't imagine a weekly standing meeting on my calendar. It was like Already making me calendar claustrophobic to see that there.
They make me very tired. And I remember when my daughter was about 4, my middle daughter, we went to check out a Montessori school and they required the parents to wait in another room while they talk to the kids. And I'm sitting in the room and I knew it was maybe halfway through. All of a sudden, Sarah sprints into the room and I said, what are you doing? Aren't you supposed to be in there? And she said, I didn't know when it was going to end. And I thought of how many times I've been in a meeting like that where you just want to sprint from the room because you don't know when it's going to end. And even if you're running it, sometimes people start grandstanding or they feel they have to justify how they spend their time in. You just know your whole schedule is off now for the whole day. I prefer to avoid them if I can.
And that is what's so interesting about running a tiny business with a loosely connected team. What I found was going from one person to a handful. I also employ some combination. Nobody full time, but maybe three core team members and a core outsourced podcast production group. Then I hire specialists along the way. And it's interesting because in a way, everyone can do their work without having regular all hands. But it's interesting to see people who want to run a tiny business not solo, but also buck convention in terms of setup and shoulds and, you know, zoom became the norm in the last few years and I just can't stand to be on video every day, all day. It's like feeling of wanting to run out of the room, particularly with video calls. I feel so chained to my desk and staring at this one little point in the laptop all day, I just can't do it.
Oh, it's so exhausting. Yeah, I don't like it either. Maybe one a day or two a day I can handle, but when it starts going above that, I feel like it's draining my energy. I think it's because you have to be so self conscious, you know, of just sitting there, always looking straight at the camera. Yes, I think it's good for client meetings. That's the area where sometimes you do have to have meetings in your business because the client wants to get to know you. And sometimes having the whole team there is good for problem solving. Like if you are doing creative work, it can be useful for that. But internally, a lot of times I think the team actually prefers Having one on one communication and they will have offline communication. I'm on a team, an editorial team where often I text back and forth with different people on the team or we'll just jump on a quick call and we just resolve things on our own without a meeting. That seems to work really well. I never really feel I'm lacking anything if I didn't have an all hands meeting. It probably depends somewhat on the industry. There might be some where you really have to have that, but I think there's more than we think that really don't need meetings.
If each person owns a very different part of the business, that's one thing. If everyone's producing the same widget, I think that's another. You know, it depends how the business is diversified. You say in the appendix. As you know, if I've read my earlier work, I love data and I know this about you, that you love data and you are the person I know who is most skilled at sifting through the Small Business Administrations annual census. I cannot make sense of the census. I think I emailed you a handful of times while working on free time because I'm like Elaine, I just couldn't make sense of it. I really couldn't. And I tried. What I found so interesting is that I love that you included all this data in the back of the book. You included all these charts of businesses with fewer than five employees, fewer than 15. I was shocked at the nature of these businesses. The book itself features a lot of people who run kind of online consulting, education, these types of companies. But the appendix has things like gambling. Copper, nickel, lead and zinc mining.
Exactly.
Butter production, cotton ginning. Were you surprised by this data of all these companies that are out there running these tiny businesses with big money?
Jenny, I was really surprised. It was so much fun at. I hate to say fun because it makes me sound like a total geek, But I have two daughters, they're 18, they're twins and they're really good at math and computer programming and that sort of thing. So the census data, it was multiple requests for information from the Census Bureau. Then we had to program this Excel sheet. What we did just for the benefit of readers who don't have the book. We figured out the average revenue and the average payroll for each industrial code in America. And we subtracted average payroll from the average revenue to see which ones had the most money left over. This isn't an exact proxy for profit. Anyone who runs a business will know that. It's just to give us an idea of which ones have that profit potential. There could be other costs, and I included information. NYU Stern School of Business compiles regular data on which businesses on the average profits of each industry. So I really recommend that people look into it further. But this is just a starting point. And yes, we broke it down by up to four employees, five to nine employees, and 10 to 19. And to give you an example, like up to four employees. And number one was casinos, number two was butter creameries, number three was ethyl alcohol manufacturing, and number four was general medical and surgical hospitals. A lot of these are not industries that everybody would want to go into. So I took it one step further. And for this book, I interviewed almost 60 entrepreneurs. And I came to some conclusions that were subjective. Based on these charts and the interviews, which would be the best industries for the average smart person to get into. My categories were E commerce, business to business. E Commerce showed up a lot in the charts across the different size categories. Souped up service businesses. And what I mean by that is it's not just a trading time for dollars. Jenna Kutcher is an example. She's.
She created courses to teach people how to do photography. But where she really makes her money is as an Instagram influencer. She shares her photos on Instagram and she's built a huge following and she gets advertising revenue. So that's the souped up part of it. It's taking a very creative approach to the service business. Then there's manufacturing. These days, the average person can become a manufacturer from their living room as a solo entrepreneur if they want to, using tools like Alibaba to find outsourced factories. One example I loved was Jeffrey Stern. He's a guy in his 60s, he lives in Connecticut, and he makes the voice boxes for the little bears in Build a Bear Workshop. And those greeting cards, we've all gotten those musical greeting cards that when you open them up, they make a sound. And he's run the business sometimes with contractors. Currently it's all contractors, but he's had employees, and it's about a $4 million revenue business. What I really took away was we all live in places where we drive down these routes and you pass these ugly industrial buildings and you have no idea what's going on inside of them. But there's probably someone who's making millions running these things, and they've been very creative as entrepreneurs. Maybe the business itself is not that exciting. Being an Instagram influencer would be. But some of these, like manufacturing, wholesaling, aren't. But entrepreneurially, they're allowing people to have these great lifestyles. But sometimes they do require a team. Even if you don't own the factory, there might be some warehousing or things like that. So that's that I'm writing about in this book and I think just poking through those charts, it's fascinating to me. My kids, when we started getting the results, they're like, mom, you're chuckling like a lunatic. And I was, because it was so funny to see which ones came out on top.
I know you mentioned souped up service businesses. I didn't see too many. I thought I would see so many more in the charts for photography, consulting, coaching, all these things. Because at least online and I think in the circles that you and I spend time in, even going back to Tim Ferriss four Hour workweek, there's so much buzz around these types of businesses. It's hard for me to picture a gambling operation with fewer than five employees, but there they are.
You know, when I think it is gas station casinos, I've been poking around to find that out. Where are these businesses? Because there's so many different ones. With the service businesses, it tends to be things like accounting firms in the charts, those types of businesses, more professional attorneys. But they usually have some sort of engine to go beyond what you could do in a normal two person attorney firm or three person firm in accounting. They have some digital component to spreading the word. Maybe they're doing webinars or other things. I remember a few years ago I write for CreditCards.com sometimes and I had to attend a webinar and pay like $300. I think it was, it was about some new change in credit card law. And There were these two attorneys in Washington D.C. who are probably the world's leading experts in this little niche of credit card law, which is extremely complex. And I get on the call and there are 600 people on this call, all paying the $300. And then I see they're airing it two more times and I thought, wow, if these guys were seeing clients who had questions about this change in the law, how many could they actually fit onto their calendar? Now they've scaled their messaging way beyond what they do in their client work. They can still do the client work, but they've added on this component. They spent a little bit of money to hire the webinar company to do it professionally. But those types of add ons are really available to anybody who has expertise. And it's a matter of seeing what other people in your industry are doing. Being a little creative about it. You could develop a course, an online course, maybe not in a change of credit card law, but something else, like how you run your legal practice or using Zoom and the law, whatever it may be. If you're doing something interesting that other people ask you about, a lot of times it can be turned into some sort of informational product. That was a category that came up in the million dollar one person business, my first book. But I found it's even more possible to do it in these businesses with teams because each person might have some sort of secret sauce that could then be productized, and that's where you're selling things repeatedly. Another interesting example, this was more of a product driven business. It's called Black Paris and the founder is named Julian Ohayon. And he's kind of a global citizen. He seems to always be in a different location every time I speak with him. It's a clothing brand aimed at young men where all the clothes are black. The idea is simplicity. And what he introduced was a digital product. If you have an iPhone, you know how you see all those little icons and it has a background. Well, his is all black, as you might predict. And it's a digital product. And he said once you've covered the cost of creating it, the profits are almost 100%. And so when he added that on to his business, in addition to the sweatshirts and things like that he sells, his profits went through the roof. So that's another thing to think about. Even if you're selling tangible products, maybe there's a digital product related to that that you could hire professionals to help you develop that's tied into your brand that you could sell through different channels. There are all kinds of platforms out there for selling these things and improve your profitability. There's some upfront costs. You and I were talking about the upfront costs of producing a book. I mean, you have an investment on the front end. Once you sell it, the work is done. Basically your work is only promoting it at that point.
Yes. And that's the whole idea of creating assets for the business. And I find that even creating a sales page, a really well done sales page, is an asset, as well as creating the info product itself.
We'll be right back just after this.
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Going back to these souped up service businesses, which I think probably applies to a lot of listeners, find a way to charge premium prices by delivering unusual value. And you give the example of Laura Belgrave's shrimp club, people who do some combination of masterminds but that over time the ones that you've seen grow these big businesses while keeping their team small do find a way to charge premium prices. And I would just love to hear a little bit more about that. I think it's not surprising to hear you say that and write that, and a lot of us deep down probably know, but I would imagine that entrepreneurs often are just pricing things too low and that these big businesses got to have some chutzpah in a way to go big with their pricing as well while delivering the massive value that generates that level of pricing.
I'll get to Laura Belgrave also because she has some interesting methods, but there's a couple in the book, tiny business, big money that has a brand called Nomad Lane. It's Kish Vasnani and Vanessa Jaswani is his wife and they created a travel bag. She actually started the business as an Etsy store where she was selling different creative products that she came up with and she found that all her travel products were the most popular. She had a little travel pouch and one of her pet peeves was when traveling with a laptop bag that fit under the seat, everything would get lost in the bottom of the bag. So she created this bag that had a zillion pockets to keep every single thing you can imagine organized. And they initially priced it at like $100. And then they experimented with the pricing and they found that it sold better at $200, which was really interesting to me. There's sort of a psychological advantage, I guess people were telling them they were undercharging for the quality of the bag and that of course made the business much more sustainable and profitable. Laura had an interesting approach. She worked with a Business coach. She was actually charging really high rates. She's a great copywriter, she's hysterically funny. She had worked in the TV world and she was able to raise her rates to $1,450 an hour. But there was a catch, which was that was a lot of pressure. When somebody's paying you almost $1,500 an hour, you have to be brilliant every time. And sometimes being a human being, maybe having an off day that day. And she was starting to feel really stressed about having to produce at that level on every call. So she started cutting back how many hours she would do a week. And then working with the coach, she had created these two PDF courses and one of them was about how to create a good About Us page. She hired an artist to nice it up. And I love that. It's just how she speaks. She's just got a great way with words. And the coach said, you're barely promoting these PDF courses. Why don't you do more email marketing around them? And that became a big engine that helped her grow business. And then she added on other things like a mastermind. And the combination of those things allowed her to eliminate almost all of the one on one client work, except for occasional favor for an old client. But it took a lot of the pressure out of the business and it took her time to experiment and figure out what really worked for her. I think that's an important lesson I took away was it's not just making money. This is about a business that you love to have. And if you're making $1,500 an hour, but it's giving you agenda and you can't sleep and you're dreading every day that you have to do it, it's not worth it. Because life is about more than money. You have to have a purpose. And there's a lot of ways to execute on your purpose. For her, the courses and the mastermind allow her to do something similar to what she was doing in those client meetings, but without the stress. That's another component. I know you and I have talked about that a lot, how to create a life that you love. And I would like to interview you about that. But I think that's one thing that I found in these case studies is there was sort of an evolution where people got to know themselves as a business owner and what do they like and what causes them stress. And then they got closer and closer as they evolved the business to their ideal business. And it might not be the same for somebody else in the exact same niche.
Another significant differentiator is that this transition these business owners and companies make into more sophisticated systems and automation. And I remember talking to you about this book before it was out. You were saying that was one of the big differences of going from one person $1 million business to a tiny business big money category really. Systems are a linchpin of that. It's almost impossible to scale and particularly to have a team without some measure of systems and consistency specifically around automation. You challenge readers to try to free up one day a week through automation. I'm just wondering if you've seen any particularly creative examples recently or even one in your own life that freed up a lot of time for you.
I'll share is Tiffany Williams runs Rich Girl Collective. She's an entrepreneur herself, was initially involved in using Teespring to sell T shirts. She's got a Yorkie called Prada and she just loves Yorkie. She created a Facebook community around that and then she got into Amazon selling and as she grew the business she wound up using a bunch of different automated tools and I included her list in the book because I thought it was so good. Her favorite tools were Adobe stock for stock photos, Canva for graphics, click Funnels. That's an online marketing tool. Convertkit, which is an email marketing platform that helps creative professionals deepen their relationship with their fans. Podia, where she hosts her courses and then txt180.com, it's a text messaging service you can use for marketing with your customers. And she saves a lot of time. She actually had a battle with cancer in the middle of running the business. She's a young woman. She needed time to recover and she didn't want to totally close the business and was able to use all this automation to keep it growing. And then she wound up adopting a baby. She's healthy now, but I think about that how life giving the automation really was because it allowed her to have a high level business and still get the rest that she needed while she was going through her treatment.
That's really inspiring. That's what the work is planning for times that we're out unexpectedly for reasons all across the spectrum. That's one thing I appreciate and that drives me toward having a tiny business that doesn't just revolve around me is that it's so stressful being the bottleneck that if any of us were to get sick or need to take time away, even a creative pause. It's really stressful that all the income grinds to a halt and that's always what keeps me reluctantly growing a team. Because if I had it my way, I probably would work solo most of the time. But I just don't like the result that if anything happens, the income stops flowing.
That's the hard part of freelancing. It's really important to take stock of your business and think about that. Like, okay, if I got sick for three weeks and my income stopped, does it really have to be that way? Right. Could I have a product that is bringing in revenue whether I'm functioning well or not? A lot of people need a mental health break after two years of COVID If you just have burned out completely, like a lot of people have, and you want to go on a yoga retreat or something, can you even do it when you need it? Maybe you just need more fun in your life. I mean, fun is really important right about now. Especially if your business doesn't allow you to do that. That's an opportunity to take inventory. I'm actually doing this in my own business because you and I were talking before about this. Things kind of creep up on you. You start adding maybe a new line of business and you're doing a lot of it manually. And you never take time to stop and think about o what are the things I'm falling behind on? Could I use a tool to do that, or could I hire an admin or somebody to handle that for me? And then all of a sudden you're just grouchy and overworked.
That grouchy factor, yes.
One of the things I do with my business coach, his name is Doug Wick. He mostly works with middle market CEOs. I found him to be very helpful. He has me put all my hours in a spreadsheet to see what I'm doing. And if there's anything I can do that could be outsourced or could be automated. And I think that's a good practice to really take a week every hour of the day. What are you doing? And could that be done by somebody else? Sometimes you do things manually, so to speak, that have other purposes. For instance, I could probably hire somebody to drive my son to karate. But I really love that car time because we have four kids and I don't always get to talk to him one on one. And we have really good conversation. So it takes me an hour to drive him there round trip. But I get a lot out of that. I think he does too. So I wouldn't want to hand that off. Even though technically I could be working that hour doing Something else that's really meaningful. But I love that time with him. So there might be things that you do that maybe washing the dishes yourself is your form of meditation. You don't have to take everything out of your life that you do that someone else could do. It kind of forces you to think about are you getting something out of how you're spending your time. If you're doing something that you hate, it doesn't involve anything that enriches your life in any way, then don't do it. That's the stuff you want to offload.
I've made a point over the years to look at every stream of income and ask how to scale it. Because I think like you said, sometimes we add things and it feels like we have to be right in the middle of it or the bottleneck. And then if you just ask the question, I found just the open inquiry of how can I pull myself out of this stream of income now that it's established A do I want to keep doing it at all? And then B, what other solutions are there that don't involve me and my time? So going from having my own one on one coaching clients to now having a team of coaches, everybody wins, they get referrals and revenue. And I just reached a point where I didn't want the meetings on my calendar. As much as I loved coaching, I did it for 10 years. It was my most steady stream of income. There reached a point where it was more important to me to work on the business and do one to many communication and not one on one behind paywalls, so to speak. It's nerve wracking to pull out of some of those activities, but I felt like I wouldn't know what was possible in terms of growing my book and podcast if I didn't give myself the chance.
I think that's a really important point, Jenny, because we evolve over time. Ten years is a long time and the person you were 10 years ago May have been different in terms of what you wanted out of life. Maybe you really needed those one on one relationships with the coaching clients at that point. But I think it's important to keep challenging ourselves and allow ourselves to reboot and refresh the same way we might clean out our wardrobe because what we were wearing 10 years ago is out of style now or you just don't like it anymore. Thinking about that, how have I evolved as a person and does my business allow me to be the person that I really am now, not 10 years ago? Life changes can happen. Maybe you get married or you have a child and what you want out of your work is completely different. Maybe you value flexibility above all else because you had a child, then the children are out of the nest. Maybe you actually want the in person time with people because now you don't have a constant house full of people and you crave that human connection. A lot of things evolve and I think sometimes when people burn out on their business, it's because they're not letting go of a revenue stream that they really should because it's no longer connected to who they are right now.
If you could give fellow micro business owners permission, what would it be?
Do less out of obligation and spend more time doing things out of love and joy. And that includes meeting with clients. The more you gravitate towards the people that energize you and the activities that energize you, the more your business will thrive.
Do less out of obligation, more out of love and joy. A Woman after My own Heart Elaine, thank you so much. Where can people find you if they want to keep in touch?
Thank you Jenny. I invite anyone who would like to get in touch to connect with me on LinkedIn under my first and last names, Facebook or Twitter. I'm on all of those under my full name. It's in the show notes. Hard to spell.
Yep, I'll put them right in the show notes.
Please write. It makes me a better journalist to know what people are thinking about and where they have questions. So I do write back and I always enjoy hearing from listeners.
Awesome. And make sure you get your copy of Tiny Business Big Strategies for Creating a High Revenue Micro Business. Elaine it's always a joy to chat with you. It's one of the things I love doing more of. So thank you so much for being here and thanks everybody for listening.
Thank you Jenny. I feel the same. Thank you for all that you do for your listeners because what you're doing is really empowering them to live that life of passion and joy.
If you've listened this far, you get a gold star.
Thank you.
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