30 min read
Solo Startup Guidance: Nuggets of Wisdom from A Seasoned Serial Entrepreneur
Joe Rando
:
May 14, 2024 11:20:06 AM
We usually don't start the episodes by listing off all of the accomplishments of our guests, but when you have somebody on who is this impressive and accomplished, it’s hard not to brag a little bit, especially when he has so much advice for solopreneurs. Mind you, this is us bragging on his behalf, he doesn’t seem like the kind of guy who would do that.
If you aren’t familiar with Rob Walling, it’s time to get familiar. He:
- Is a serial entrepreneur who has started six companies and has had multiple exits
- He runs MicroConf, the largest conference for bootstrapped startups
- He has written four books about startups
- He has more than 15 million downloads on his podcast
- He’s invested in more than 170 startups (including WP Engine and SparkToro), but doesn’t believe the only way to start a SaaS company is to raise money
And of course, he’s just a really cool guy and was open to all the questions we had for him that relate to helping you run a company of one.
In this episode, we discuss things like:
- The key advantages to bootstrapping a startup versus seeking outside funding
- Common pitfalls that aspiring solopreneurs encounter and how to avoid them
- Strategies for solopreneurs to achieve profitability sooner rather than later
- Trends shaping the future of solopreneurship
- The most crucial skills or qualities that solopreneurs need to succeed in today's competitive landscape
Plus the one piece of advice he would give aspiring soloprenuers, and so much more. Be sure to tune in.
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Connect with Rob Walling
Favorite Quote About Success:
"The harder I work, the luckier I get." - Samuel Goldwyn
Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr's SoloSuite Starter gives you free education, community, and tools to build a thriving one-person business.
So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, click here to check out SoloSuite Starter!
About Rob Walling
Rob Walling is a serial entrepreneur who has bootstrapped and sold multiple startups, most recently Drip.
He runs MicroConf, the largest conference for bootstrapped startups, has written 3 books on startups and talked for more than 670 podcast episodes about building a startup in order to build yourself a better life.
He co-founded TinySeed, the first startup accelerator designed for bootstrappers, after watching thousands of founders struggle working nights and weekends with no funding alternatives that would allow them to simply build profitable, "real" businesses.
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Episode Transcript
Carly Ries:
Okay. I usually don't start the episodes by listing off all the accomplishments of our guest. But when you have somebody on who is this impressive and accomplished, it's hard not to brag a little bit, especially when he has so much advice for aspiring solopreneurs. Mind you, this is me bragging on his behalf. He doesn't seem like the kind of guy who would do that.
Carly Ries:
So if you aren't familiar with Rob Walling, it's time to get familiar. He's a serial entrepreneur who has started 6 companies and has had multiple exits. He runs micro comp, which is the largest conference for bootstrap startups. He's written 4 books about startups. He has more than 15,000,000 downloads on his podcast, and he's invested in more than a 170 startups, including WP Engine and SparkToro.
Carly Ries:
But he doesn't believe the only way to start a SaaS company is to raise money. Needless to say, he has a lot of experience. And, of course, he's just a really cool guy on top of it and was open to all of the questions we had for him that relate to helping you run a company of 1 because he himself was also a solopreneur. So in this episode, we discuss things like the key advantages to bootstrapping a startup versus seeking outside funding, common pitfalls that aspiring solopreneurs encounter and how to avoid them, strategies for solopreneurs to achieve profitability sooner rather than later, trends shaping the future of solopreneurship, the most crucial skills or qualities that solopreneurs need to succeed in today's competitive landscape, plus the one piece of advice he would give aspiring solopreneurs. We talk about this and so much more, so be sure to tune in.
Carly Ries:
You're listening to The Aspiring Solopreneur, the podcast for those just taking the bold step or even just thinking about taking that step into the world of solo entrepreneurship. My name is Carly Ries, and my co host Joe Rando and I are your guides to navigating this crazy, but awesome journey as a company of 1. We take pride in being part of Lifestarr, a digital hub dedicated to all aspects of solopreneurship that has empowered and educated countless solopreneurs looking to build a business that resonates with their life's ambitions. We help people work to live, not live to work. And if you're looking for a get rich quick scheme, this is not the show for you.
Carly Ries:
So if you're eager to gain valuable insights from industry experts on running a business the right way the first time around, or want to learn from the missteps of solopreneurs who've paved the way before you, then stick around. We've got your back because flying solo in business doesn't mean you're alone. Okay. So before we jump into this episode, I just have to share this new free offer we have called the SoloSuite Starter. Being a solopreneur is awesome, but it's not easy.
Carly Ries:
It's hard to get noticed, and most business advice is for bigger companies, and you're all alone until now. LifeStarr's SoloSuite gives you free education, community, and tools to build a thriving one person business. So if you're lacking direction, having a hard time generating leads, having trouble keeping up with everything you have to do, or even if you're just lonely running a company of 1, be sure to check out SoloSuite Starter at Lifestarr.com and click on products and pricing at the top menu. It's the first one in the drop down. Again, it's totally free, so check it out at Lifestarr.com
Carly Ries:
Click on products and pricing, and it's the first one in the menu. Hope to see you there. Rob, welcome to the show. We're so excited to have you.
Rob Walling:
It is my pleasure. It's great to be here.
Carly Ries:
Oh, this will be so fun. I'm not gonna lie, though. You're kind of intimidating to talk to. It's like going through your history and all of the companies that you've helped grow and then exit successfully in your investments and all these businesses, it's kinda like, you're a big deal. I'm gonna call you very big deal on this show.
Carly Ries:
And it's funny because I wonder I mean, looking at your background, I don't think
Carly Ries:
you would always be our, typical guest on this show because you've worked with such large companies, such big budgets. But what a lot of people don't know about you is that you were also a solopreneur and you lived that life for many years. You were over your corporate job and you wanted to fly solo. And that's what a lot of people, who listen to this show are are experiencing today, and they're just starting out. And so I kinda wanna take your experience with these big companies, but also as a solopreneur and whittle it down to this solopreneur audience because I think you have so much advice to share from all of your experience.
Carly Ries:
So if you're ready to go get going, I'm ready to get going.
Rob Walling:
It's very kind of you, and absolutely, let's dive in.
Carly Ries:
Awesome. So actually, a number of people in
Carly Ries:
our community, I do wanna start with the bootstrapping. A lot of our audience doesn't go after funding because they're coaches, consultants, but there are those people that are looking for outside funding, but you are you're all in it for and you're you're pro investor, but you're also pro bootstrapping. And I wanna know what the key advantages are in your opinion for bootstrapping a startup if people are needing that money or or versus seeking outside funding if they're needing more money?
Rob Walling:
Yeah. I've thought a lot about this. I've actually given several talks. I wrote about it in one of my books.
Rob Walling:
I have this loose rule of thumb. So you've heard of the 80 20 rule where it's like 80 20 applies to a bunch of things. It's not exact, but it's directionally correct usually. This is similar. I call it the 1 9 90 rule.
Rob Walling:
So I think that if you're starting a product company of some kind, so not consulting, not agency, not freelancing, but a product, whether it's software product or or something else you think can grow quickly. In my world, it is, you know, SaaS and software. I think about 1% of those companies should consider raising venture funding, which is like the go big, go home. I'm gonna get, you know, raise a lot of money and go big. I think about 9% of them should consider raising, not venture, but some type of funding to help them get along.
Rob Walling:
So maybe angel funding. I run a startup accelerator for SaaS Bootstrappers called Tiny c. Like, it's independent funding where you remain in control. You don't have to get huge and sell for a 1,000,000,000, but there's still some type of investor involved. And then the other 90%, if you remember, it's 1 9 90.
Rob Walling:
The other 90%, I think should just bootstrap. What what I think they should just bootstrap. And the thing that kills me is when I go on the Internet or I used to go to in person meetups where I grew up in the in the Bay Area. And the expectation was that just a 100% of companies raise funding. And that's just not true and it's not even smart.
Rob Walling:
Most companies shouldn't raise funding. And boost funding is just a tool. Funding is like a hammer or a or a a shovel. And when I see people bootstrappers get too caught up in funding's evil. You should never raise funding.
Rob Walling:
It's like, so you're saying I should never use a hammer? But what if I have a nail? Right? Sometimes you should use funding. And then the VCs or the venture industrial complex as I call it, they wanna they want all of us to raise funding because that's how they build their ecosystem.
Rob Walling:
It's like, well, I don't wanna always use a hammer. What if I have a screw? Or Or what if I'm trying to pick up snow? You know, then I should use a different tool. So that's kinda how I view it.
Rob Walling:
There's, a balance. I think the the biggest benefit back to your question is, like, bootstrapping, you remain in control. You can do it nights and weekends. You can do it while you have a day job, and you don't have to ask anyone for permission. That's the biggest thing is I hate seeing entrepreneurs, solopreneurs, single founders, whatever waiting around to be anointed by some investor.
Rob Walling:
Go build your company. Go build your business, not your slide deck. That's what I tell a lot of folks. So I think you can bootstrap until you're able to raise funding. You know what I mean?
Rob Walling:
The best slide deck if you're raising is revenue. So go out and sell something.
Carly Ries:
I could just create a really long bumper sticker
Rob Walling:
Print it on a t shirt or something.
Carly Ries:
Really long. Yeah. Such good words of wisdom. So for people that are so this 99% people that are bootstrapping, obviously, there is a right and wrong way to do it.
Carly Ries:
What are some challenges you see people face or some things that you see people doing wrong when it comes to bootstrapping space?
Rob Walling:
To bootstrapping? Yeah. Well, number 1, I do see way too many people who should be bootstrapping, who are instead waiting around asking for permission, pitching investors, saying, well, once I get funding, then I can build a business. It's like, no.
Rob Walling:
Don't do that. I've already I've already governed that. I won't belabor that point. Another mistake I see is people who want to, quote, unquote, play business. It's like, I have business cards.
Rob Walling:
I'm gonna go get a logo for on Fiverr or Upwork. I'm gonna incorporate. I'm gonna get an LLC. I'm gonna set up bank account. And it's like, how about you get someone to pay you money?
Rob Walling:
You don't have a business until a customer or a client, I mean, whatever word we wanna use for them is paying you some money. And so if you're selling a service, like the first service that I sold was I was at software developer at my day job and I realized that people might pay me $50 an hour. This is a while ago. It was probably a 150 now, but it was, like, 20 years ago ago to, like, write some code or build a website for them nights and weekends. So I posted to Craigslist.
Rob Walling:
I am a developer in Los Angeles. $50 an hour and I didn't really know what I was doing, but someone paid me a thing. I had no LLC. I had no business cards. I had no logo.
Rob Walling:
But guess what problem I solved? It was a problem that someone needed solving. Right? And I made my first $1,000, you know, on the side that way. Or you can, you know, let's say you wanna build products, like, you can go in your basement and try to to, you know, write an ebook or build a course on something that you know.
Rob Walling:
But instead of spending 6 months doing it, can we get out a quick minimum viable thing that we put on Udemy to see if if there's interest in it? Again, it's a mistake of people who I think are avoiding the hard things. The hard and scary things are the rejection of no one wants to pay for what I've built. I don't like talking to people and I'm scared. That was me for sure.
Rob Walling:
But so it's that resistance. You know, Seth Godin talks about the resistance of shipping something into the world. That's probably, aside from asking for funding, like, one of the biggest mistakes I see folks making.
Joe Rando:
It's kind of a fail fast approach. Like, get it out there, see what's working, what makes sense.
Carly Ries:
Is that how you say would say people can overcome that fear? Like, just to do it and just to dive in and to experience that feel? Because that's such a mental block for people. How how can they overcome that?
Rob Walling:
Yeah. I think so I think part of it, honestly, is becoming well, you I know we're gonna talk a little about kind of community and networking a little later, but being around other people even if it's online, like, you don't have to be in person with them, who are shipping things and succeeding and failing and you start to see how it's done and, oh, this is possible. I I I know several freelancers who are now making, you know, $20,000 a year on the side nights and weekends, in addition to their day job, and you see what the realities of that are like. Like, seeing other people who have done it before you is a huge, to me, a huge bonus. And so whatever you're looking to do, if you wanna be a bootstrap SaaS founder, you should go check out MicroConf.
Rob Walling:
If you wanna be more of a lifestyle hacker, go to indiehacker.com. If you wanna be, you know, a coach, like a life coach or an executive coach, go to coaching.com. Right? If you wanna be a a digital nomad, go to, the dynamite circle. Like, there is a community for pretty much everything that you wanna do.
Rob Walling:
And obviously, you have a solopreneur community, so be around other humans that are doing it. And you wanna see those that are succeeding and failing and you wanna learn from them a bit and you wanna learn just enough and then you wanna ship. Don't learn for 12 months. Don't learn for even 6 months. Learn for a few months and then take a plunge and ship something and, you know, usually what happens though you think the worst case is that someone rags on it.
Rob Walling:
Someone says this is a crappy product or your idea is dumb. The worst case is and the most common case, no one cares. No one even notices. That's actually what happens with most products.
Joe Rando:
And, as you as you say this, it's like when you when you go out there and even if you get that negative feedback, if somebody cares enough to to give you feedback, at least they're telling you something. Maybe they're telling me you're going in the wrong direction, but, you know, that's valuable. I mean, I've launched companies. I launched a company, and we had this core product, and this was it, you know? This was what it was all about.
Joe Rando:
And by the time we were done and we sold it, we had sunsetted that product because it was too hard to support and built out an entirely different set of infrastructure that was actually what created the value on the company. So you just don't know where you're going to wind up when you start putting these things out there, but the market will tell you if you ask, I think is what you're saying. Is that fair?
Rob Walling:
Yeah. That is what I'm saying. I'm also saying start smaller than you think you need to because people will look at, a huge software company who could we name? Slack, HubSpot, Zoom. Salesforce and be like, well, so I'm gonna compete with them. And it's like, woah. Woah. Woah. Woah.
Rob Walling:
They're here, but they are public companies. They have raised hundreds of millions if not 1,000,000,000 of dollars. They started 20 years ago. How about you launch something really small? If you really wanna do software, you really wanna do information like write a small ebook, write a little add on to Shopify or a little add on to HubSpot, you know, go in their app marketplace, like, get something out in a month and feel quickly.
Rob Walling:
I see first time entrepreneurs especially thinking that the way to do this is the way that these massive companies have done or these big successful, you know, entrepreneurs. Like, you have to stair step your way up. I talk about this a lot where it's like start small, build something, launch it in public. It may not support you full time, but then build on that. And over time, you gain the reps.
Rob Walling:
You put in the reps and you get the experience to be better at it.
Joe Rando:
It's all about doing what they're not doing. Right? Or the holes that they're leaving, the little cracks.
Rob Walling:
Yeah.
Joe Rando:
I love it. Yeah. that makes so much sense because if you try to go head to head, you'll you'll lose. You will lose. You know, there's no way.
Carly Ries:
Speaking of, so you talked about community, and I know we wanted to talk about that a little bit. And it's the the community and network is such a huge deal for these one person businesses. But the other thing that we try to tell people is that you don't have to do it alone. This community can also be collaborators and partners and all these things. With the remote workforce, what advice do you have for people that want that help and how, like, and how do they approach collaborations and and make it so you're helping each other rather than flying solo?
Rob Walling:
Yeah. I mean, I think there's so there's 2 things I would think about as a solopreneur. And like you said earlier, I was solo for 5, 6 years before I started an effort that was large enough that I needed to hire employees. So I lived it. And there's 2 categories.
Rob Walling:
Right? You're talking collaborators which is folks like, hey, let's work together. And then there are I would call them freelancers, contractors, team members, you know, where I'm managing them. I'm hiring them and I'm paying them dollars per hours to do a task. So I wanna start with the latter because I honestly think if you can, like, that's where I started.
Rob Walling:
Because to me, collaboration's always got just a little complicated with, well, who gets the lion's share of this? Who's bringing in the work? Is there a contract that we're you know, it's like you start having not cofounders per se, but there's a lot to work out with that. It's pretty crystal clear if I go on Upwork or I go on Fiverr, I go on freelancer.com, and I say, I'm gonna pay you $20 an hour to do x y z thing, and we have it in writing. I'm gonna pay you $50 an hour to do x y deliverable.
Rob Walling:
Even that can be complicated. Right? Because, people sometimes are flaky. I think my big learning there was in order to find, like, my first virtual assistant I hired in 2000 let's think. That was not 20 years ago.
Rob Walling:
It was probably 17 years ago. I think I hired 4 over the course of 6 months before I found one that was really good. But then I worked with her for, like, 3 years. You know? She was part time in this and that.
Rob Walling:
So big learning there for me was you're not gonna get it right the first time, but learn how to delegate and, you know, how to hire well enough and then just you gotta fire fast, in that respect. The collaborators is a is a different topic, but I what I learned was I could get I could get to a certain point on my own, but I at a certain point, I wanted to grow bigger companies. I wanted to be more ambitious, and I knew that I needed more than just me. And so I actually took on a cofounder in 2012 and launched you know, that was my big big startup I did.
Joe Rando:
Did d you know that before it became a big problem, or did you figure it out in advance?
Rob Walling:
I figured it out as I went. I wanted when I left my day job, really well, I think it was the last salaried employment I had was, like, almost 20 years ago now. And I said, I will never again work with other humans unless it's just me hiring someone to do a task, total task based freelancer stuff. And I'm gonna only I'm gonna hamper the growth of my business. I'm gonna keep it at the level where it's just me.
Rob Walling:
And I had at a certain point, I had 9 contractors. There were designers and there were 2 virtual assistants. There were people with support and then, you know, I had multiple small software products. I had about a almost a dozen small software products that all cobbled together made, like, just under it was about a 150, $175,000 a year. It was a great living.
Rob Walling:
I lived to the 4 hour work week. I worked about 10 to 12 hours a week for almost a year with all these small software products and this team of of contractors. And so I was like, this is it. Rest of my life. I'm semi retired.
Rob Walling:
You know? I was like, in my early thirties or something. And what I realized to your point, Joe, was I got I got 2, 3 years in, and I was like, man, this is pretty lonely. I got 4 years in, and I was like, this is actually really boring. I got 5 years in, and I was like, I wanna do something more than this.
Rob Walling:
Like, this is I found freedom. You know, I believe, like, we we all seek freedom, we seek purpose, and we seek relationships. I think those are the 3 things that keep us healthy. I found freedom. I spent my whole mostly, you know, up my adult life up until then finding it.
Rob Walling:
Once I had it, it was great for about a year until it was like, no. I've lost purpose because I just have these things generating money. And I'd realized if you're listening to this, you probably think this guy's insane.
Joe Rando:
Not at all.
Rob Walling:
Everybody I know who's hit this where you get bored. You need that. If you're an entrepreneur and you're ambitious, like, folks on this call and people listening to this podcast, like, you wanna take it to the next level. So that's where back to your question, Joe, of, like, did I real I it took me a few years to realize, oh, I think I do need collaborators or in my case, it became a cofounder with my next EMAX effort.
Joe Rando:
It's interesting though because we talked to someone yesterday, on a podcast, and he basically, his business got to the point where he was getting killed, and finally realized he had to start hiring people. But you, it was the other way around. You realized that your meaning in life was getting overrun by loneliness, and decided at that point to start bringing other people in. Very interesting. I like this.
Rob Walling:
I would still consider my I know I don't know if you consider someone with 9 contractors a solopreneur, but it it was weird. I didn't. Yeah. I didn't have a team. They were all just they had tasks and they just did them.
Rob Walling:
And so I still would call have called myself solopreneur. And the reason I did that was because, man, I didn't wanna answer email support for all these products. Right? It was like, that would have been terrible. That would have been a big mistake.
Carly Ries:
Well, so, Rob, you had that was a key learning, like, the loneliness and everything. And I think it's helpful for people just starting out to hear kind of some challenges that people have overcome in their careers, especially somebody that has had a career like yours. What other key learnings would you say you would want to share with solopreneurs who are just starting out that you could help them avoid?
Rob Walling:
Yeah. I think I touched on the one earlier of, like, the the biggest thing I see is people not people avoiding the hard things. The hard there's no question if you're listening to this and you have a skill set, whether you're a software developer or whether you're a writer or whatever, you can go write an ebook. There is no risk that you can't. There is no risk you can't build the software product.
Rob Walling:
There is no risk you can't build the product. The risk is will people pay for it? Can you sell it? Can you market it? So you almost you wanna reverse it and try to answer those first as best you can.
Rob Walling:
And so sometimes that means, oh, I'm gonna put up a landing page. Like, if I'm a marketer, I'm gonna gonna try to put up a landing page, write some copy, try to drive traffic to it, see if anyone's interested in this thing before I build all of it. You know, maybe, hopefully, most of it. If I'm more if it's gonna be a sales thing, if I'm a freelancer doing consulting, which I did, I'm gonna put myself out there whether it's Craigslist, Upwork, Fiverr, what a Facebook, you know, Facebook groups, whatever that, hey, I do this thing for this much per hour and try to sell it first. Try to put yourself out there in a way that can get you, you're trying to remove the uncertainty, you know, around that.
Rob Walling:
Early entrepreneurs do too much and not hire anything out. That's probably the other thing, and that was an early learning as you can tell by my 9 contractors.
Joe Rando:
What was your first thing that you outsourced?
Rob Walling:
It was, email. So for me, again, it depends on what type of product you have, but I had these I was I was a developer who learned how to market. And so I was doing SEO and AdWords and stuff, and I was driving traffic to a couple different software products and there was a lot of support. It was low dollar, low cost, high, number of customers. And so there was this constant email support coming in.
Rob Walling:
So I hired a virtual assistant who would answer all those email responses. And then as I figured out what else she was good at, it turns out she could, like, do some design work. So she would design little things here and there for me. Oh, I learned she could write emails, so she would write emails. But she became a utility player for me.
Rob Walling:
But realistically, it's to me is I look at my business and I think, what are all the things I'm doing? And is there anything I really don't like doing or I'm not good at? And is there anything that's a bottleneck that I have like, I have too many incoming leads. I'm doing too many sales calls. Well, maybe I need to, like, find someone who can help with sales calls.
Rob Walling:
Or I have too many customers. I need help with customer success and getting them onboard. Well, maybe I need to hire a customer. So, you know, it's that's it it really does depend on the business and the type of business you launch, but it's always looking at what are the bottlenecks and what am I not what am I not good at? What's sapping life for me?
Carly Ries:
Rob, I'm curious. You've been in this entrepreneur space for nearly 20 years now and I'm sure there have been so many changes. I mean, obviously, with the remote workforce that's changed everything. But what have you seen change the most that would apply to solopreneurs? And what do you predict, like, the next 10 years could see your solopreneurship?
Rob Walling:
10 years is a long time, but I'll do my best. No. 5 years. I'll tell you the 2 things. Looking back, the 2 biggest shifts were when Skype became essentially free.
Rob Walling:
There was no there was no easy way for me to call someone in Bangkok, Thailand in 2,004 or 5. It was very expensive. Right? And I think Skype launched around there, you know, maybe the executives. That changed a lot.
Rob Walling:
And especially you could then do video because then you could look someone at the eye and actually have a relationship. That's when the second thing kicked in. It was offshoring. It was being able to hire someone in Bangkok, Thailand or in the Philippines. My first VAs were in the Philippines.
Rob Walling:
That all happened. It felt to me like it started happening and I think I had my first VA in 06. 4 hour work week came out in 07, and it really blew up from there, for the next 3, 4 years. A lot of folks were doing that. And I remember there was all the hubbub about offshoring and how that was gonna, you know, ruin.
Rob Walling:
Every American was gonna be out of a job and everything and that obviously, you know, wasn't the case. But looking back, those were the things. It was, and there were a bunch of digital nomads around that time that moved. Right? It was, like, disenfranchised angry, like, kids coming out of college who couldn't get a job that even paid for their student loans.
Rob Walling:
They would move to Bali or they would move to Bangkok. And the fact that Skype existed, they could then do remote freelance work at half the price of my friends in LA because at the time I lived in LA, and yet they were Americans with fully fluent English, you know, so they, like, were still able to do it. So, anyways, Skype in that communication, obviously, now it's Zoom, but you you get the idea, as well as offshoring slash outsourcing slash just being able to hire someone that didn't live in your city. And, frankly, my early businesses that I talked about, all my solopreneur stuff, none of that would have worked if I hadn't been able to hire cheaper talent. Because everyone I knew in Los Angeles made a lot of money and I couldn't have built a business, you know, without it.
Rob Walling:
Now that's looking backwards. Looking ahead to me, it's AI. Like, AI is the superpower. Right? And learning to use it, whether you're learning to write prompts well, AI doesn't do everything for you, and AI is an accelerant.
Rob Walling:
It is not an advantage unless you learn to use it better than your competition. Right? But anyone can go to Chat GPT. We could go right now and just type stuff up, outline a YouTube video that is compares, you know, Superman and and Batman. And it's gonna put out a mayonnaise sandwich, which is very bland and not actually that interesting.
Rob Walling:
So then it's like, okay. How do I either get better at writing prompts or how do I have the knowledge in my own head that I can turn that into something unique? So to me, it's learning whatever whatever it is in your field and how AI applies, whether it's AI that helps you write code, whether it's AI that helps you, you know, outline, brainstorm, do whatever, generate images, You know, it is I think ignoring it or, like, putting our head in the sand and acting like it's not a thing is is not gonna get you ahead.
Carly Ries:
Yeah. And it's funny to say to speed up. So full disclosure, chat GPT helped me with these interview questions. I was I was going back and forth in my head because there's just so much I can ask you when it comes to entrepreneurship. You have such, a history.
Carly Ries:
And I was like, I need to really whittle these down. So I came up my with my questions and then I put it in Chat GPT and I, like, was kind of playing tennis with Chat GPT to come up with the right questions as it applies to our audience. And it's just because I feel like people just look at it as a content generation tool, a code generation tool, and it's used for so many things to save you time that would benefit you for your time to be put elsewhere. Because I wanted to make sure we had best questions for you for our audience, and it was, like, kinda like an like, an assistant. Yeah.
Rob Walling:
That's what I've used. I've had to name you know, naming things is hard. Right? Naming books because you kinda can't especially books, you can't change them. Right?
Rob Walling:
So this is my 4th book. I'm currently writing my 5th book with my wife about selling selling companies. Naming them is hard. I now my first stop, Chat GPT. So I'll ask Chat GPT do 20 titles that are alliterative just to see because I can't come up with 20 titles.
Rob Walling:
And and usually, one is like, oh, that's interesting, you know, and you're just going down a path. And that's what I mean. Like, I'm not mister super pro AI. I know there are issues with AI and image generation. And is it stealing people's images?
Rob Walling:
Kind of. I think the courts are gonna work it out. So I'm not like some AI bro, but I do think that putting your head in the sand is not the right response either.
Joe Rando:
But I agree. It is so good for naming things. I struggled with naming things and it's a great tool for that. I'm with you.
Carly Ries:
Well, so people have AI now as in their back pocket. They can use that to you said to use it better than competition. I think the hard thing right now is, like, with coaches, with consultants, there are a 1000000 coaches and consultants, and it's separating themselves from the crowd. And in this virtual age, you can have a client in Timbuktu or in your local city. And so it's really hard to stand out in this space.
Carly Ries:
So AI aside, what advice would you have for solopreneurs to stand out from their competition?
Rob Walling:
So the way that I've typically done it in my career is to, a, find a position in the market that I think I'm the best at. And it has to be different from it may be different from all. That may be tough with coaches, but different from most. So it's not, hey. I'm I'm the next CEO executive coach.
Rob Walling:
I'm a life coach. It's like, I'm a life coach for men in their early thirties who are struggling with their career day to day. I'm the executive coach for founders of, software companies who are doing, you know, who are teams of 10 to 50 employees. It's right? It's like you start to niche down.
Rob Walling:
And the fear there, of course, is, well, aren't I shrinking my market?
Joe Rando:
And Yes.
Rob Walling:
But can you be the best in your state, in your country, in the world at that one thing? Maybe. And if you are, I mean, think think of my like, what I do. I you could say, oh, Rob's in the startup space. Right?
Rob Walling:
I talk about startups. Startups is huge. Startups is Uber, SpaceX, Tesla. Those are startups. I don't do any of those.
Rob Walling:
So it's like, okay. Well, maybe are we just talking about software startups? And it's like, even just software startups, There are, like, software startups that software that powers drones, software that runs on, you know, on an eye, you know, on on a phone or, like, powers my little amp here that's running my microphone, like, embedded. So I don't do any of that. I'm web software.
Rob Walling:
Okay. So that's even smaller. And then there's web software that's not SaaS. I'm only SaaS. And then there's bootstrappers, venture like, think of how small I've made my market.
Rob Walling:
I mean, the entire addressable market of my whole world is probably a couple 100000 people maybe in the world, 2, 300,000 at any given time. So it's not very big. And yet, I've built 6 successful companies, you know, bootstrap 5 of them. Like, I have a venture, you know, an accelerator venture fund that invests in them. I have a community for them. I'm working on my 5th book. Like, it's big enough. So that's kind of the advice I've been giving.
Joe Rando:
It's like, do you want do you want 10% of a small market or 0% of a huge market? You know, and that's what happens when you go too broad. And, you know, so you're you're you know, we're we're all preaching the same thing here. It's like, please focus, niche down, and people are so reluctant to do it.
Rob Walling:
And you can go broad later. I could now if I wanted to. Well, maybe I'll do venture back SaaS too. That's adjacent. Now we have a Venn diagram. I'm doing what I'm doing and then Yes. Well, I could branch into venture. I would have credibility now. And then maybe I do non SaaS software. I could if I wanted.
Rob Walling:
I don't have much of an interest in it, but that like, you can do that later. It's a it's like a land and expand or a wedge. There's a bunch of terms for it kind of in in MBA land.
Carly Ries:
And you can kinda do trial and error to figure that out. Even for us, we rebranded to the podcast to the aspiring solopreneur for the one person business because at first, we were going after solopreneurs. Well, there's, like, 50,000,000 plus solopreneurs to end up with big audience. And so we're like, okay. We have those people that have been doing this for a while.
Carly Ries:
Let's just focus on these new guys, the aspiring solopreneurs. Even that, at some point, Joe and I will probably whittle that down. We're just trying to figure out how. But, like, we were just, like, we need to cut, like, because that 50,000,000 down because we're not gonna go anywhere with that. Yeah.
Carly Ries:
It's so true. And I guess you have such great words of wisdom. What if if you could leave our audience with one piece of advice for running a company of wine, what would that be? It's to think in years, not months.
Rob Walling:
I think people come in and and they see others having success, and they think it's gonna happen quickly. And that's the quickest way to have your hopes dashed to lose motivation and to close-up shop. I say that funded companies fold or fail when they run out of money. Bootstrapped companies fail when the founder runs out of motivation. And that's what I'm saying here is how do you keep that motivation up?
Rob Walling:
Number 1, it's gonna take a while. Think about, you know, to be prepared for that. And number 2, have some wins along the way. You want some early wins. You want a win next month.
Rob Walling:
You wanna win in 6 months. Without that, without some type of reinforcement, and this comes from doing things in public. Like, I was saying earlier, like, getting a landing page up, having conversations. If you sit in your basement and try to, whatever it is, code, write, think, do whatever for 6 months, like, there is no there's no feedback. You get no dopamine from that.
Rob Walling:
And that's a problem when your entire business is run based on your personal motivation. Because as a solopreneur, that might be one of your most valuable assets.
Carly Ries:
Love that advice. This has been so great. And, Rob, that was your own advice and this is a question we ask all of our guests which is their favorite quote about success. So now you can steal somebody else's advice and and tell us here.
Rob Walling:
I love the quote and it's misattributed to 10 different people. I believe that Samuel Goldwyn said it from Metro Goldwyn Mayer, quote, is the harder I work, the luckier I get. And I just appreciate that no one I know that has been successful at anything has not worked hard for it. And some people work harder than others. Some people are get luckier than others and they stumble into a startup.
Rob Walling:
Oops. I just sold it for 20,000,000. I had a friend who did that and he's like, I got so lucky. But you know what? Also, he put in a bunch of time too.
Rob Walling:
So to me, you can not in all cases, but in most cases, you can at least accelerate your luck, create a little more of your own luck, certainly be more in control of your own success if you're willing to put in hard work.
Joe Rando:
Yeah. Hey. Before before we go, I have to ask a question. So the Batman, Superman, what what's going on?
Rob Walling:
So I'm a long time comic book collector, and I stopped. You know, I did it when I was a teenager, and there were always comic books that were way too expensive for me to afford as a 12, 13 year old. And I stopped because it was nerdy and, you know, you couldn't get, interest from those of the opposite sex, at the time. And so later, flash forward to 2016 where I sold a SaaS company, and I was went into retirement for 6 months and was kinda like, I can do whatever I want now. I started seeing a few comics come up for sale around.
Rob Walling:
I was like, wow. I can never afford that. That's 1,000 of dollars. And now, look, I have the money. So I'm like a dabbling.
Rob Walling:
It's just a hobby. It's a fun thing. But as a result, I have some posters on my wall. There's actually Wonder Woman over here too. It's the trifecta of the of the go 1st appearing golden age.
Joe Rando:
So, the we have I don't know. Do you know who George B Thomas is? George is a HubSpot wizard. He's got his own business called Sidekick Strategies, and we work together. He's a contractor, and he helps us with all of our HubSpot to market.
Joe Rando:
He hosts events. Well, George is what you are, but to the Marvel Universe. So I think we should have you guys on together to debate
Rob Walling:
The PVP battle to the death. Yeah.
Rob Walling:
Just let us know.
Carly Ries:
You are married now. So you were able to attract
Rob Walling:
I'm able to branch out. That's right.
Carly Ries:
You have the hobby too.
Rob Walling:
That's right. And I will say I collect more Marvel than DC. These are just the only covers that are available on display. So these are these are metal displays that I can change out. I totally would do Spider Man and, The Punisher.
Joe Rando:
We won't have what do they call it?
Rob Walling:
Battle to the death. Yeah. 2 men enter,
Joe Rando:
1 men leap? A slam.
Carly Ries:
Yeah. For people that are just listening, Rob has these images on him on behind him, on his wall.
Joe Rando:
So Oh, yeah. I'm sorry. Yes.
Carly Ries:
Well, Rob, I could talk to you forever. Where can people find you if they want to learn more about you?
Rob Walling:
So if folks are watching this on YouTube, they wanna head over to youtube.com/microcough. that's one of my companies that I run, and I release a new video there about every week or 2 just talking about startups and bootstrapping. If they're listening to this as a podcast, I have really the longest running bootstrap podcast, in existence called Startups for the Rest of Us. I just recorded episode 710 this morning. I've shipped 52 episodes a year since 2010.
Rob Walling:
And so it's kind of a fun jaunt. You can go back and listen to all the nutty goodness from the past 14 years.
Carly Ries:
That's so cool.
Joe Rando:
What was the first one?
Rob Walling:
Microconf Like, micro conference, shortened here.
Joe Rando:
Oh, micro conf. Okay. C o n f. Got it.
Carly Ries:
Yeah. That is so great. Well, Rob, we can't thank you enough for coming out today. This has been such a beneficial and enjoyable conversation, and we really appreciate your time.
Rob Walling:
It was amazing. Thanks for having me.
Carly Ries:
Yeah. And listeners and viewers, we love providing this content for you. We love educating you and bringing in these awesome guests like Rob in order to to do so and to continue to do so. We would love those 5 star reviews, those comments, subscribes, all of the above. You know what to do at this point.
Carly Ries:
Please do that. We'd really appreciate it. And otherwise, we'll see you next week on The Aspiring Solopreneur. You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go.
Carly Ries:
So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com
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