The Ultimate Small-Business Survival Guide (With Self-Made Boss Authors Jackie Reses and Lauren Weinberg)

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This is a podcast episode titled, The Ultimate Small-Business Survival Guide (With Self-Made Boss Authors Jackie Reses and Lauren Weinberg). The summary for this episode is: <p>"It feels really lonely to be a business owner, and everyone feels like they're starting from scratch and going through these things by themselves. Jackie and I thought that there are so many people out there that have come before the current slate of entrepreneurs and business owners, and they've all learned incredible things and are full of wisdom and insight...we thought it'd be great if we could package just some of those wisdoms and insights up and share them with other business owners." </p><p><br></p><p>That is how <em>Self-Made Boss</em>, a book covering nearly every aspect of the life of a small-business owner, was born.</p><p><br></p><p>In this American Dream episode, Jackie Reses and Lauren Weinberg, co-authors of <em>Self-Made Boss</em>, join Elias to talk about what they learned by talking with small business owners across the country. Plus, Lauren, who is also the chief marketing officer at Square, shares marketing pro tips to help navigate today's dense social media scene.</p><p><br></p><p>Be sure to hit the subscribe button to get new episodes when they drop every other Tuesday.</p><p><br></p><p>In the meantime, be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with Elias, Jackie, and Lauren on Twitter at @eliast, @jackiereses, @WeinbergLauren and @DriftPodcasts.</p><p><br></p><p>For more learnings from Elias, check out his quarterly newsletter, The American Dream. You can subscribe at</p>

Speaker 1: Welcome, everyone, foreign language. Today, I have a little bit of a different episode for you. Usually we're used to hearing about entrepreneurs, people in tech and in their journey and other tech leaders that have achieved their own version of the American dream. I love sharing those stories because I want to be able to share stories from everyone, but I'm also aware that many of you are in the throes of starting a business, right? The dream in many cases, not always, is about becoming an entrepreneur, becoming a self- made individual, right? That's what every immigrant... I felt I wanted to become. So today I'm talking to two leaders who wrote a book just for you. Jackie Reses and Lauren Weinberg are the authors of Self- Made Boss, a book that crowdsources tips, hacks, and advice on how to start, run, and grow small businesses from the people who actually have done it. You can think of it as part starter kit, part encyclopedia, and part inspiration. Welcome Jackie and Lauren to the show. Thank you for being here. You mentioned that you decided to write Self- Made Boss based on conversations you were having with Square customers. Can you explain what were those conversations that trigger for you to say," We have to capture this information." Maybe start us off, Lauren. What do you think?

Speaker 2: Yeah. So in my role running marketing at Square, we talk to customers all the time and I think never more so than during the pandemic, leading into the pandemic to understand how customers were feeling. But I would say just as a general rule of thumb, we like to stay really close to our customers. Just see how they're doing, see how they're feeling, understand what's top of mind for them. I think that there was themes that sort of bubbled up all the time. One is... and I also ran my own business before I went to Square so I had a lot of empathy for some of the challenges that we hear, but there's a lot of the same challenges that everybody's going through. One is just a lot of people feel like they're reinventing the wheel. They're always starting from scratch, figuring all these things out. When in reality, there's millions and millions of people who have come before them. We also heard from a lot of our customers. They wanted to be connected to other business owners so they could ask these questions, and just one little question about something, that takes a lot of their time. We know that small business owners literally wear every single hat, so people start their business because they're passionate about something or maybe it's something that they inherit in their family. Then let's just say, for example, that you start a bakery because you love to bake, but all of a sudden you're now the master chef, you're also the CFO, you're also like the head of hiring. You need to deal with legal and tax and it's just a lot that business owners everywhere have to contend with. So I would say just based on the fact that A, it feels really lonely to be a business owner and the fact that everybody feels like they're starting from scratch and sort of just kind of going through these things by themselves. Jackie and I thought," Well, there's so many people out there that have come before the current slate of entrepreneurs and business owners," and they've all learned incredible things and they are full of wisdom and insight and they've done things a lot of different ways. I think one of the things that I love the most about small business owners is that they're just so gritty. They're putting together hacks and they're just constantly coming up with ways to solve problems, and we thought," Wouldn't it be great if we could just package just even some of those wisdom and insights up and share them with other business owners, but do it from the perspective and the voice of entrepreneurs. So it's not coming from Jackie or from me or from somebody in academia. It's really just coming straight from the mouth of people who are on the ground, living these experiences every day.

Speaker 3: I had this amazing experience. So I was in Cleveland, Ohio on a tour of the country. I had to stop to Cleveland. I met with a woman who owned a cupcake store, and a husband and wife who were older, who ran a hot dog stand. We had this small business forum. There were a bunch of politicians in the room, economic development, and then these entrepreneurs. I remember the hot dog stand guy who was probably 65 years old saying," I had this fluke. One of my kids made me do an Instagram post. People came in at the lunch counter and found it funny and I couldn't believe that people saw my Instagram post." He said," Then I started to do more of them and I'd get more of a following. Then I realized people were coming in and following changes in our menu and they'd laugh. Then I realized I was driving lunch traffic." So here you have this person who is the least likely Instagram influencer, runs a hotdog stand, talking and explaining to these other entrepreneurs, how to do social media marketing. There were two observations from that. One is these small business owners are incredibly insightful and they have wisdom to share. It just might not get packaged up in the same format that a Fortune 500 company CEO goes on to CNBC and expresses their profound wisdom that they learned at Harvard Business School or Wharton. But I'm telling you this wisdom is equally genius. Then secondly, they really need to hear it from each other because it's hard to get pragmatic tips from good sources. So listening to other entrepreneurs is super powerful. I'm sure your podcast audience understands that because they can learn something from everyone they listen to. So I think those observations made the book come to life in a way that felt very real for the people in it and the people who are reading it right now.

Speaker 1: Yeah, absolutely. No, I can relate to it in so many ways. I was doing a podcast with the SoftBank portfolio companies and so this is SoftBank, right, and they were looking for advice on how to launch into a new market and whether a podcast was still a thing or whether something... they were talking about logistics and I asked them... I find out that truck drivers are part of their audience, like that would help their business. Right? I said to them," That sounds like a fantastic audience. They're locked in the truck to listen to podcasts. You can do a three hours and you can crowdsource from them and just go out and meet them where they are, where they eat, where they sleep, what do they need? What are the issues? What are their challenges? Because no one is creating content for them and they would totally love it." So just like the hot dog stand. Yet these are startup people with millions of dollars in funding and could use the advice from this guy with the hot talk stand because he created an audience, he grew it and he helped his business. Right?

Speaker 3: It's interesting. So the book is organized by chapter. One of the chapters we have is on operations and logistics. We have four small business owners in there. Peter Stein, Jonathan Chabika, who runs an olive oil company, Latonya Cokely, Lisa O'Kelly and Elon Pasal. They all run different kinds of businesses. One is a ice stand, an ice cream stand in New York. One is a gel company out of Hawaii. One's a restaurateur. One's an oyster farmer. One owns a olive oil company. One of the interesting stories about operations and logistics came out of the pain of the pandemic, which is Sciabica's Olive Oil. They noted behavioral change. So your behavior changes when you're buying olive oil in the grocery store versus mail order. So they've found this moment of a platform shift when people were changing their behavior patterns from buying olive oil as a daily staple to being more willing to go buy a specialty product from a unique purveyor that specializes in olive oil. So they took advantage of that, but they talk about how they had to completely redo their packaging in order to take advantage of post office rates. So they redid their workflow at the most micro level and were able to get time and steps and cost out of that experience. So it doesn't matter whether you're FedEx or whether you're Jonathan Sciabica in an olive oil company in Northern California. They understood how to translate challenges into everyday operational execution. I think they're really good stories that are very pragmatic of how do you get going? How do you change your workflow to make that work? It's hard to go read that in a traditional textbook and say like," Ah, I got it. I can translate down to my business in the same way that some of these entrepreneurs did in the stories that we tell in the book."

Speaker 1: Yeah. That story reminds me of... what is it called? The Founder? Did you watch that the McDonald's movie?

Speaker 3: No, but I know what you're talking about.

Speaker 1: So there's a movie, The Founder, where they show how the actual creators of McDonald', they went to a tennis court and they kind of drew in it the kitchen until they can make the burger as fast as possible, as efficiently as possible. Right? They would just draw it with chalk on on the tennis inaudible and then they were like," Okay," and they would say," Okay, now move. Okay, now go here. Now go to the next station. Now put the ketchup, now put the bread." Right? Because they were trying to figure that out. So that was the beginning of fast food, of not having to create something.

Speaker 3: We tried to translate it into real.

Speaker 1: Exactly.

Speaker 3: You're a plumber, you're a hair salon, you're a restaurant, you're whatever. How do you translate these things? Because you're not immune to it if you're a small business. It's not like you're immune to strategy, HR ops, marketing, financing. All of those things you have to learn. So the more you pay attention to it and see other examples at a micro level, the more that you realize you have to think through all of these challenges.

Speaker 2: Yeah. I'll add to that too that we... I think were really intentional in who we picked to be part of the book, and so we have business owners from all over the country from every different kind of industry. So Jackie mentioned we have oyster farmers, we have olive oil manufacturer, ice cream stores, we have hair professionals, stylist, consultants, dentists, you name it, roofers, everybody, in every type of industry from all backgrounds also in the book as well. The idea being that there's somebody in here and maybe it's not particularly in the chapter that... you could read the book from beginning to end or you might say," You know what, I just really need to focus on hiring or marketing right now," and go to that chapter in particular. But the idea was that there's somebody in here that every business owner can really identify and relate to.

Speaker 1: Yeah. I mean, I think my perspective and what I focus on the American dream, especially with immigrants and Latinos, Blacks is to be able to show options and be able to give them access to opportunities. The goal is not to tell everybody learn to code and go start a billion multi- billion dollar company. Right? I mean, I want that too. I wish that on anybody that wants to do it, but it's not for everyone. Right? We know the failure rates in that. My goal is for people to achieve that... when I first came to this country, the advice that I was getting from people was like," Go work at..." I worked at McDonald's. I cleaned offices, worked at McDonald's. Then people were like," You should work at the post office because it has a great pension plan." Or they said," Go work at UPS. They might have better benefits." Right? What I want to give options to people is," Okay, there's those jobs, but what if you could start your business?" Right?

Speaker 3: So in this country, there are 30 million small businesses. 23 million of them are sole props, meaning they're a single person. Interestingly, out of that, if you were to characterize who owns companies and just put it in your mindset, like," Can I do this?" There's one group of people that do it to manage their lifestyle. They can make the amount of money they make. They get by on their life. They're very happy. They are managing their lifestyle so they have control of their life, but they have enough money to get by. There's another group of entrepreneurs who are trying to build and turn it into something big and they're starting it. They want to grow it. They want to go build a big company. That's a very distinct group. So you can be either. So I think that's the interesting dynamic and we write a lot for both so that you can be the person who just wants to have a tiny little one chair hair salon. That's just fine. But you still need tips on what kind of image you're going to present and how to raise financing and how to manage your business bank account. So I think all of those things are important and included in the book Self- Made Boss.

Speaker 1: Customer service, right? Be able to create it into a subscription, be able to follow up. For example, I do spend a lot of time talking to my mechanic. Right? We discussed a lot about his business and there's different types of support to a small business owner. There is the emotional support. There is the theory, the knowledge, which is operational logistics, marketing, finance, hiring, firing, et cetera. But there is also the emotional, which is hard, and then there's strategy. So when I go pick up my car and because he knows I'm in business, he usually starts picking my brain and we get to talk about it. Sometimes I'm giving him the idea to turn his business into a subscription business, just basically as all his top customers to just pay up front for the year, and then you have that budget to fix a car.

Speaker 3: The issue I always found, I raised with the people who entered my home orbit was why don't you take credit cards? They all say," Ah, I don't want to pay the few percent," and I'd say," But do you know how hard it is to go chase me down? You know I'm a good customer, but I'm away, I ran out of checks. I didn't have time to do this," and thankfully companies have moved well into that orbit. Lauren should probably talk about that, but I'm amazed that's one of those issues where more small businesses don't truly appreciate the value of cash flow.

Speaker 1: Yeah. I mean, Lauren, tell me about this. For example, one of the things that I saw hurting a lot of the Latino... there's east Boston here, a huge Latino community and they were very cash focused, cash businesses, right? They couldn't even apply for PPP during the pandemic, they did not know go to online. So I did a couple of webinars for them where we talked about different technologies they could use. Can you tell me more about create advice on that aspect of why switch to digital to currency?

Speaker 2: Yeah. Well, I mean, first of all, I think that there's definitely, as Jackie mentioned, this perception of," I don't want to pay the fee." I think what businesses don't account for is lost business and also just the value of their time. Chasing people down for money I think is just not a good use of time. So one of the things I think that I'm a big proponent of is all business owners should embrace technology. I think if you think about what's happening right now, I, for example, when we talk about people coming into your home, I moved during the pandemic like a lot of other people. I saw this chair online, I had to call the company, turns out that the guy who was making the chair was a Square customer and then he said," Okay, hold on, let me go get my Square reader," and I said," Why don't you just use invoices? You could send me an email invoice"." He said," Really? Tell me more about this." So I sent him a tutorial video and I said," I'll be your guinea pig customer," but then this just saves you so much time. People can place an order online. The previous way that they were getting paid is you had to call them. I think a lot of people don't want to call anybody. They don't want to talk to anybody. They just want everything to be seamless. So I would say my big piece of advice is that businesses should really embrace these solutions. The good news is that there's a lot of companies, Square included, but so many companies that have realized, to Jackie's point, that there's 30 million small businesses in the United States alone and more every year. More people are starting businesses now than ever before. There's a huge opportunity within the Latinx community, so many different communities, and I think if these business owners think about embracing technology from the beginning, if you think about the things that are really plaguing businesses today, it's access to capital and it's much easier to get a loan when you have sort of this history of transactions that you can show. The second thing is staffing and hiring. There's a lot of ways that technology can help you automate. You can automate your payroll, you can automate your invoicing, you can automate your marketing, your follow- up messaging, and all of these things are things that you then no longer need to hire somebody to do. So I would say that I think more businesses need to think about... we like to call it at Square the total cost of ownership and I think the thing that probably most business owners do is they underestimate the value of their time.

Speaker 1: Yeah, absolutely.

Speaker 2: And the time that they spent on all these little tasks that they could actually automate. I think there's just a little bit of resistance and fear of giving up that control and letting technology do this part for you. But I would say I highly encourage everybody to... a lot of these solutions are also free, by the way. Try it, see how it goes. I think if you run a restaurant and you're struggling with staffing, like almost every restaurant is today, bring in QR codes that allow people to order directly from a QR code. If you're short on wait staff, this could really literally make the difference between seating at 50% capacity or 100% capacity.

Speaker 1: Yeah, absolutely. I just went yesterday to this place called Taqueria Jalisco. Maria is the owner, love her to death. She's streamlined the process. Before they won't come to the table. Thank God now she's open, right? So we can actually sit, very small place, but now you come in and you can take orders online. She had some menus there, but it's streamlined. She goes," The menus are right there. You go to the register, you order and I'll just bring it to you." They completely changed from that too many steps process that there were before. Everything is served to go, it's just streamlined and she goes," Thank God. I'm really happy." I go," How's business? How's everything?" and she's like," Thank God, no complaints from me. Everything's growing. The only one's complaining other people in the kitchen cooking." She goes. That's what she said. I agree. Technology is a big, big enabler. I'll tell you as a technologist, creating a good user experience for everyone to use is really difficult. That's why I think they lose some of the hope. Tell me a little bit about... I think you said part inspiration, right? I think it's important to... one of the carrots out there... there's two parts to starting a business. One is failure rates are really high. I want to talk a little bit about that, but what should people be expecting to go towards so they know when they reach success as a sole proprietary ship, for example?

Speaker 3: So when do people reach success?

Speaker 1: What does success look like?

Speaker 3: I think it gets to that comment I made earlier. There are two archetypes for business owners. One is the person who's completely fine managing their life. That could be a person who's a tailor that's retired that earns that extra$50, 000 a year as a tailor. It could be a restaurant owner who makes a million dollars a year in the restaurant. I think it really depends on your own goals and your own needs. So I don't think there's any one dynamic that illustrates success for anybody. I think owning a business is an incredible journey and you are putting yourself out there and you'll have stress associated with managing your life and managing your finances in a way that having a standard W2 job might not create. So people do it for their passion and their freedom. So it really depends on how you prioritize your own goals as to what it looks like. I think that's the benefit and I think that's what's going on now with the great resignation. People are saying," I know how to do this thing. I'm tired of working for someone. I want to own my own thing and I'm willing to kind of put the time and effort in in order to make that happen." I think we're seeing people devote their own mental energy to their own passion. It's awesome. It's absolutely awesome.

Speaker 1: Absolutely. I'll share two things. I love your advice or your tips on this, but I don't know if you're aware of this. But at least in Massachusetts, because I'm involved with the community here, there's a study that's been recently. I think this study might be nationwide, but Latinos are one of the fastest growing segment in the sole proprietorship in the entrepreneurial aspect. So when they do the surveys, they're finding that they're the fastest growing number of entrepreneurs and it's not peculiar to a specific industry either. It's like they see that across all segments. So that's exciting. However, the stat against it is that at least in Massachusetts, the average small business revenue for the whole state is about 800,000 a year. But when you go to Latinos, it's about$100, 000 a year, total revenue for the year. So that's the issue that we're dealing with.

Speaker 3: Well, it sounds like a lot of sole props.

Speaker 1: No, in the SMB though, I'm saying. A sole prop that is not Latino, it's 800, 000 and a sole prop that is Latino average is 100, 000.

Speaker 3: Wow. Wow. Didn't know that stat.

Speaker 1: That's the world that we live in. Because the lack of information that your book has, it limits how to grow the business into a way that generates that kind of revenue. At$100, 000, we cannot survive.

Speaker 3: So one of the things that I think we've found is access to credit is a key unlock for small business owners. So one of the dynamics that I think helps underrepresented people get loans is that around using credit facilities associated with technology tools. So it could be American Express owns a small business lending company, Square owns a small business lending company into it. There are all these companies that now have credit associated with your account. So once you start running point of sale, like Toast in the restaurant business, for example, Stripe has it. Once you start running your business on these platforms, you're able to start getting credit. I find there are two dynamics. One is if you have a business that does$ 100,000 like you're describing, your loans are usually too small to get at a traditional bank. It's probably going to be a$ 3, 000 loan. Realistically, 4, 000. You can't get a loan like that at a traditional bank, but you could probably get it on Toast or Shopify or Square once you're processing$ 100,000. So there are some really interesting dynamics there associated with affiliated and using technology tools that can help small business owners unlock access to credit. The good thing is it uses data, you don't have to know anyone at the local community bank. It's completely algorithmic and I think that benefits underrepresented people who might feel like they're not connected to that community of financing. So I see it as a huge opportunity for underrepresented small business owners to kind of gain access to the type of credit they need to grow their business.

Speaker 1: That's a fantastic tip, right? Because whenever you ask a small business owner or a business owner in general, what's one of the most important things you need to grow, and it's capital, right?

Speaker 3: We have a whole chapter in the book on it and the chapter is called how to manage your money, get loans and get paid on finances. So that's kind of the ethos of the book, is like," Okay, here's how you get a loan. Here's what you should do." It's super pragmatic. It is not like save X for reams of paper for a year. It's go to your online platforms. You also could go to a traditional bank. Here's how you do it. Very, very pragmatic.

Speaker 2: Yeah. I would add also that right now, what's interesting is that... and I think coming out of the pandemic people really want to see their communities succeed. I think maybe before the pandemic, you took that for granted a little bit because there was a lot of businesses in your community and they were just there and they were doing okay, and then the world shut down and everybody started to think about like," What would my community be like without..." your favorite taqueria or whatever it is that you really love about your community. So I would say businesses should also just embrace this idea of community, come together within your community, and I think this is something that you could see even like some of the Latinx businesses doing as well, which is working with each other, spreading the word. I think the appetite is there and people do want to support businesses in their community. So I think capital is one of the biggest challenges for businesses, hiring is challenging. But the other thing is marketing and spreading the word and thinking about where to spend your time and your energy and how do you really create that? The best way to get your business up and going is through an organic flywheel where you don't have to pay a lot of money. So these business owners should be thinking about every single touchpoint that they have with a customer, whether that's the sticker on their window, their customer support, or however they're interacting with people as a brand experience. If you wow people with that experience, they're going to be much more likely to talk about it, and then business owners can take that and then just kind of grease the wheels a little bit and give their business owners fun tools and ways that they can support them to help spread the word and help them really grow their businesses. Because the appetite is there, right? People do want to support their local businesses and even within underrepresented communities, I think that is probably even a stronger sense of really wanting to see those businesses thrive. So I think that people don't like to ask other people to spread the word or to help them, and I would say they should. They should ask for that. Because I think at the end of the day, a lot of times people do want to spread the word and pay it forward and they just don't know how. So make it really easy and I think you'll see those results really pay off.

Speaker 3: You know what? Lauren has incredible insight on how small businesses do marketing calendars. We should talk about that because it's a really cool topic. I've been super impressed to learn it from her and I think it would be really helpful to the audience.

Speaker 1: Please tell us, Lauren, about the calendars because people think marketing is hard. It is in some ways, but it's a matter of putting in the work and people just expect that... it's like you do one video and it's just viral. Right? But tell us about this calendar because it sounds like discipline.

Speaker 2: Yeah. I think it's discipline and it's patience. So I think the thing about marketing is it is a lot of work and I think the thing that trips most businesses up is knowing where to start. So I always get asked the question like," Should I be on every social platform? The answer is no, you probably shouldn't because that's a lot to manage and you can't create one piece of content that works across all of them. You really need to be thinking about what you're creating in a way that's going to be really natural and authentic to what people are seeing on that platform or they're just going to skip over it. So I think a couple things. One is know where your audience is and really invest the time in one or two platforms and not all of them. I think trying to do all of them is just sort of a recipe for disaster, because I don't think you can do them all well. You could realistically take up your every hour in the week if you try to do that. So know where your audience is, and some of this is a little bit dependent on the type of business that you own. Right? Obviously Instagram is a very visual platform. It's also a very shoppable platform. TikTok with videos, right? I think that's something where we see health and fitness people in that industry can do a lot of content and post videos there to really build their audience. So know your audience and also what type of content's going to resonate best for your business type. Then the last piece is make a calendar and really break it down. I would say if you want to think about posting three to five times a week, let's just say three, right? If you're just getting started and you have a lot of other things to do, you pick your one or two platforms and then you can just create a calendar. I think it just makes it a lot more manageable, right? One day a week could be... first of all, I'll just start by saying that people really love to hear the backstory. Why did you get started? Why do you do what you do? Then I think just kind of create that emotional connection with your customers because the more they feel connected to you as a human and as a business owner that's doing something and the reason why you got started, I think just the more likely you are to build loyalty over time. So that's one great avenue is just talking about who you are, your background and your story. What makes your business unique? You can also showcase your employees. I think when we think about diversity, if you have a diverse employee base, then you should be talking about those employees and letting them share their stories. That will just create, I think, more interest and more people that see you kind of showing up in that way and then also want to be a part of that. Then you could pick a day where you talk about promotions or community events, and if you break it down to," Okay, three times a week and I know what I'm going to do," I think it just makes that so much easier as opposed to sitting in front of your Instagram every day and thinking," I need to create a video today and I don't know what that's going to be." I think that could be very paralyzing because there's just so many directions that you could go in with that. So that's my advice, which is limit your platforms, develop your calendar and then just do it. Right? You have to just put in the time and then be patient because you don't just build a million followers overnight. Even when you're building out a podcast audience, right? It takes time to build an audience and you got to put in the work and then you got to wait.

Speaker 1: The thing is that, yeah, I think we can talk about this for hours. It's weird. I'm the chief technology officer, so I'm an engineer, but my company, Drift, I think it's done a very special job. Dave Gerhardt and David Cansel, my partner, CEO, are genius marketers, right? So I got to watch them build a podcast before we had built a product and I would be like," Why are you guys going to the room record that podcast? We got to build a product and this is what's most important," and didn't realize that they were building a community, they were building a brand and that it took reps and sets to get that podcast to audience. Everything that you said is so... I just want people to pay attention, to play this back, everything you just said, Lauren, because it's gold. People are always looking for that answer, that silver bullet, right?" Just tell me, just tell me the answer," and you just gave them the answer. You just gave the audience the answer. But they need to dissect it and they need to pull it together and understand what you said. For example, people don't realize that if you get a thousand people in a mailing list, you can build any kind of business you want. I mean, you do not need more than a thousand people in a mailing list. You don't need 100,000, you don't need a million. If you get the right 1, 000 to follow you, if you're a plumber, what else do you need than more than a thousand customers? You cannot service more and you will make more than 100,000 a year. So people don't understand-

Speaker 3: Well, even in the book we have stuff like there's a photographer who talks about how do you photograph your blue collar activity, and What should you put on your website? Again, it's this notion that some people think that they don't need to do it because they're a certain type of business and we're making the argument there's always a way to present a visual representation of what you do. If you're a plumber, you could show yourself in action and show the professionalism of your office. You could show what your office looks like. You could show your employees. It's really nice to be able to present that amazing image. We have a woman in here, Latisha Hanky, who runs ARS Roofing and Solar in Oakland and she presents an incredible image on her website of herself. She does charity, she lists that, you see her team. You get a sense that there is more to her company than just transactional roofing and you get a sense that these are reliable, strong, good people based on how they present themselves on their website.

Speaker 1: We are humans and humans are drawn to people and we're drawn to stories. That's the bottom line. So back to Lauren's words, right? When people say like," What should I post about?" You don't need to invent anything new. I've been fortunate, right? I've been featured in so many different things and I'm like," What is it that everybody always ask me?" They want to hear my story. Everybody that inaudible on LinkedIn, they want to hear my story and I'm like," I don't want to tell my story again," but then I say it again and people want to hear it. Every business owner has a story. You just gave another hack. If you're tired of telling your story, rotate your employees, rotate your customers. I mean, it's like people are worried like,"What do I say?" There's infinite things to talk about right in front of you and yet people think it's hard. It's like, no, just make a calendar." I'm going to talk about it on the first week. I'll be the story. Then the second other story will be employees. Then it will be just a customer after I service them. Can we just do a quick recording what we did, what we solved, what was your problem, who are you?" People will want to hear the story of the customer and that is infinite number of stories. So it's just that simple, right? You just said another big thing there that people might not know. You do not have to talk about the business. You do not have to talk about the product or the price. Just be yourself and people will connect with you. Then they'll ask," What do you do? What do you sell?" Right? It cannot be in your face," Buy this, buy this, buy this." Right?

Speaker 2: Yeah. I mean, there's a time and a place for all of those messages, but I think that kind of very transactional messaging, it does come into play. Right? I think at the end of the day, people need to understand what you're offering. What are your products and services? People are price conscious, so you need to include that information, but that's not how you build a brand and that's not the place and how people really connect with you. So those things matter and I think especially now, probably more than ever, people are price sensitive and conscious, and we need to be aware of that, but that's not the thing, right? At the end of the day, it's like they want to feel that connection to you as a business owner and to your employees and what you're doing that's different. It could even just be if you own a restaurant or a food company, how do you source your food? Where does it come from? That's really important to a lot of people too. Right? They want to know if you're supporting local farmers in their community. So there's so many places to go and I think to Jackie's point, what we tried to do in the book is not just in marketing and not just in operations, but across all of these things. Because that's the big thing, right? Which is if you own a business, you are without a doubt wearing at least 10 hats a day, right? Not a day goes by where you're not wearing all of those hats and we're just breaking it down into step by step practical guide, just here's something that you can do today. The other thing is at the end of every chapter after we talk about... and this book is stories, by the way. Stories of business owners. Every chapter starts with a story about one particular business owner to sort of lead into it. At the end of every chapter, we just give you five or six questions that you can think about so you can take what you've heard from somebody else who's in business, and then think about how does it apply to your business in a way that makes it really practical. I think ultimately Jackie and my goal is that for every person that reads this, if this helps them just do one thing better in their business and that one thing increases their chances of being successful, we will feel like we have won, to be honest. That is the goal of this book is we've both run businesses, we've talked to thousands of business owners, we know how hard it is. There's just so much in here that can be really useful and helpful and breaks down these really overwhelming topics like marketing and how to secure a loan into just very practical tips and something that you will read this and you'll come away and think," Okay, I know how to do two or three things differently in my business today that will help me in the future."

Speaker 1: Thank you so much. I think that it is a worthy mission and I think you will be successful because there is a thirst for this kind of information, right? Especially in the communities that I participate on. Well, we highly recommend this to the audience. Go get this book. It's Amazon, everywhere. Self-Made Boss.

Speaker 3: There it is. Self- Made Boss.

Speaker 1: Yeah. Go get it and get those tips. But most important, like I said before, and I said it on Twitter the other day, if you want to start a business, just start the business. Right? That's where it all begin and then go get the book. Don't think about it. Start the business and then you'll have all the tips you need in this book. Thank you, Jackie. Thank you, Lauren, for being on the show.

Speaker 3: Thank you. It's been a pleasure.

Speaker 2: Thank you so much for having us.

Speaker 1: Thanks for listening to the American Dream podcast. Make sure to hit subscribe so you never miss when a new episode drops. If you like this episode, please leave a six star review wherever you listen to your podcast. If you're interested in learning more about my American dream mission, subscribe to my newsletter linked in the show notes.


"It feels really lonely to be a business owner, and everyone feels like they're starting from scratch and going through these things by themselves. Jackie and I thought that there are so many people out there that have come before the current slate of entrepreneurs and business owners, and they've all learned incredible things and are full of wisdom and insight...we thought it'd be great if we could package just some of those wisdoms and insights up and share them with other business owners."

That is how Self-Made Boss, a book covering nearly every aspect of the life of a small-business owner, was born.

In this American Dream episode, Jackie Reses and Lauren Weinberg, co-authors of Self-Made Boss, join Elias to talk about what they learned by talking with small business owners across the country. Plus, Lauren, who is also the chief marketing officer at Square, shares marketing pro tips to help navigate today's dense social media scene.

Key Moments:

  • (1:19) The conversations that inspired Jackie and Lauren to write Self-Made Boss
  • (7:51) Operational and logistical learnings from an olive oil company amidst a global pandemic
  • (10:20) No business is immune to the need for operational excellence
  • (16:10) Why Lauren thinks all businesses should embrace technology
  • (20:19) How to determine what success looks like for your business
  • (23:22) Access to credit is a key unlock for small business owners
  • (28:10) Social marketing tips from Square’s CMO

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Buy Self-Made Boss

Today's Host

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Elias Torres

|Co-founder & CTO, Drift

Today's Guests

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Jacqueline Reses

|Co-Author, Self-Made Boss
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Lauren Weinberg

|Co-Author, Self-Made Boss