Episode 768 | Reacting to Controversial Startup Advice

Rob Walling:
You’re listening to Startups For the Rest Of Us, I’m Rob Walling. Every week on this show since 2010, I’ve been showing up sometimes with a co-host, sometimes on my own to talk through what it’s like to build ambitious SaaS companies. And in the early days as SaaS was just becoming a thing, we also talked about downloadable software and mobile apps and even sometimes content websites and e-commerce sites because at that time I was running the Gamut info products, there was all kinds of stuff. But over time, this show honed in on SaaS software as a service because SaaS, especially B2B SaaS is the best business model in the world. And that’s why myself and the tens of thousands of listeners of this show, as well as the guests that you hear appear on the show, go all in on building incredible companies that bring us freedom, purpose, and relationships and that we can build and create and bring into the world without sacrificing our health, our family relationships, and the rest of our lives. 

Because we build businesses to support and to improve our lives rather than sacrificing the quality of our lives and our relationships for our companies. We want to be ambitious. We want to build incredible companies, but we want to do it in a way that isn’t unicorn or bust and that doesn’t require asking anyone for permission. So today I’m going to be digging into controversial takes from Scraping Bee co-founder Pierre de Wolff, and what I’m going to do is walk through a tweet that he posted in the middle of 2024, so about eight or nine months ago, and he says, these are my semi controversial beliefs I have about bootstrapping a successful product, and he has 15 or 20 bullets that I think are fascinating, some of which I agree with, some of which has more nuance, others I inevitably will disagree with. The best part of this is I’m not telling him that I’m recording this. 

Pierre and I know each other pretty well. He’s spoken at MicroComp. He’s a TinySeed founder. Scraping Bee is an incredible business. They’ve been public about mostly bootstrapping it to millions of dollars in revenue and they’ve done very well and grown very quickly. So an accomplished and successful founder and also a prolific ex Twitter user. And so I look forward to diving into his thoughts here in just a second. Before I do that, I want to tell you about our MicroConf Growth retreat that we’re going to be holding in London. This May of 2025, May 14th through the 16th. There are only 60 tickets available and by the time you hear this, there will be less than 60. We will sell this event out, and this is a new type of event that we’re trying, MicroConf Growth Retreat where SaaS founders connect, recharge and grow with the size. 

We’re planning it at 60 people. It’s an intimate gathering designed for SaaS founders who want to build deeper connections, gain clarity on their business and experience London like never before. So there’s going to be deep networking sessions. There’s going to be a morning work session to get feedback on your business, solve roadblocks, and there will be workshop strategies in small focused groups, then afternoon excursions and a ton of founder-led conversations throughout the event. Activities include things like going to electric shuffle to play shuffleboard. I’ve actually been to that place. Relaxing Paddleboard sessions on Region’s Canal, a guided tour of London’s best pubs and more to find out more and to buy a ticket before this event inevitably sells out. Head to MicroConf dot com and look in the top NAV for events and it’s called Growth Retreat 2025. 

All right, so let’s dive in to Pierre’s thoughts. We are going to link this tweet up in the show notes. The interesting thing is X, Twitter has some weird bugs these days. It doesn’t actually show a date of his tweet, but the replies are mostly from July 11th, 2024, so I’m going to assume that’s when this tweet went live. It’s such a weird bug. Anyways, Pierre says, today Marks six years since I left my job to start my indie hacker journey. I would say they’re far beyond being Indie hackers. They’re ambitious SaaS founders. They’re mostly bootstrapped, they’re TinySeed backed. Pierre continues. We’re now making millions a year, but we started from zero many times. Here’s a list of semi controversial beliefs I have about bootstrapping a successful product. Number one, don’t waste time on a rebrand. You don’t have a brand. You have a product of barely making $2,000 a month and at $2,000 a month, I would agree with him. 

The question then, of course I think through, because I’m on a podcast, he’s on X Twitter, on exter, you have to be extremely brief on a podcast. I would then think to myself, well, when does it make sense to rebrand? And usually that’s further down the line. It’s if you basically get an MVP brand out and you’re doing 20 or 30 KA month or your brand is hurting your efforts, it’s not helping you close sales, it’s actually driving prospects away because your design looks cheap. It isn’t conveying the messaging and frankly, the gravitas or some element of your product or your business. That’s the time when I think about a rebrand, and it is very rare that I will do that. It’s only when I’m seriously bothered. Like recently, Rob Walling dot com, which I had designed in 2018, and it was on WordPress. I had that redesigned and moved to Squarespace, and there were two reasons for it. 

One was because of the site was hard to edit, and I needed folks on my teams MicroConf TinySeed to be able to spin up new landing pages and change text. And even just adding a mention of TinySeed, there was no mention of TinySeed on Rob Walling dot com. Adding a mention of TinySeed would’ve been clunky. I would’ve basically had to hire a developer, not hardcore developer, but someone who can muck around with a word pressing and I just didn’t want it. And is Squarespace the best platform in the world? Of course not, but is Squarespace really easy to edit and my team knows how to use it? Yes, and so we paid for a rebrand of Rob Walling dot com. Now I think that’s worth it. It’s Rob Walling as a personal brand, not Rob Walling me as a person, but Rob Walling dot com sends a lot of people into this MicroConf TinySeed podcast, YouTube and Books ecosystem, and improving the brand of that property will absolutely sell more books, get more people into the ecosystem. 

And you should check it out actually, Rob Walling dot com, as I’ve said 17 times already on this podcast, but you can head there. And the about page I think is probably the one I’m most proud of. I just think our designers did an incredible job, but not only of the visual design, but of the informational design. And shout out to producer Ron for pulling almost all the content for that together in just a handful of days. But the idea there is this is a mature brand. If we were to redesign MicroConf tomorrow, I wouldn’t want to because it would mean we were standing still. But enough people see that site and the brand is solid enough that at times it can be justifiable. Do I think you should rebrand every year or two? Absolutely not. Do I think you should not rebrand as Pierre says, when you’re barely making $2,000 a month? 

Yeah, he and I are locked in on that. His semi controversial. Take number two, I think I’m just going to say controversial take so I don’t have to say semi every time. His take number two is.com, dot io dot. so.ai. In the end, no one cares. I think he’s mostly right here. I think.com is superior, but how much does it matter if you’re do io dot? So ai, I don’t know. I don’t think it’s the end of the world to be honest, as long as people can find you in a Google search. And as long as, the thing that bothered me so much Derek and I both was that we used get drip.com, so people kept calling Drip get drip, and that was infuriating. And what I wished I had done is bought drip.io or drip.co, even these days, drip ly. No, I didn’t want ly but Drip. 

So drip ai, any of those would have made sense. And I think that’s the big lesson I learned from there is to get your brand or exact company or product domain name, and then the TLD. The top level domain I make is less important because for maybe a month or two before we got TinySeed dot com, we got TinySeed fund.com. That was the initial $8 domain that I purchased before I went and bought TinySeed on the secondary market and people started calling us TinySeed Fund, and that was not fun. I did not enjoy that. And the misrepresentation is too strong of a word, but it is not how I wanted people to know us. It’s confusing. And so in the end, I do agree with Pierre, although I would say he says no one cares across these. I would say.com is the clear winner. And then for the others, I just don’t think it makes that much of a difference. 

Controversial. Take number three. Don’t think a affiliation or affiliate marketing will fix your acquisition issues. It’ll just create another acquisition problem acquiring affiliate partners. 100% true. And I don’t know if Pierre found this on his own or I’ve been saying this for 10, 12 years, that affiliate marketing is enterprise sales. And this is why I say if you are going to be a SaaS founder, don’t build your audience, build your network. Because if you build a network of folks who have audiences, that’s the killer play right there. You can then go to your network, which are people that you can text or email, and they respond right away. You’re in private Slack groups with ’em, you see ’em in person, you recognize them. Maybe you’d go out to dinner with ’em and you can ring them up. And just like Sherry and I did when we wrote Exit strategy recently, I emailed John Warlow and said, Hey, John, nice to talk to you. 

I haven’t seen you in six months. I hope things are well with you and the business. Hey, Ben Chestnut, co-founder, MailChimp. Thanks for speaking at MicroConf. Would you be interested in writing a testimonial for this book? John Warlow, would you write the forward for exit strategy? Derek Sives. Hey, man, been a couple years since we chatted and we hung out in Thailand 10 years ago. Would you be willing to read my next book that I’m writing with Sherry and write a testimonial? Hey, Sam Parr, founder of the Hustle, host of my first million, Eric Huberman, founder and CEO Hawk Media. Sherry actually knows him and on and on and on. I say these names and if I didn’t know them and they didn’t know me, it would be very difficult to get them to write endorsements of our books. And if I was a SaaS founder or wanted to do affiliate marketing, it’s these kinds of people that I would be going out to saying, does this make sense for you to promote this for this commission? 

Are you willing to help me? That’s why your network is so, so important when you’re building SaaS and your audience itself is fine. It’s an initial leg up, but your audience isn’t big enough to build a viable SaaS business on. And so back to my point about affiliate marketing being enterprise sales, it’s basically you going out and acquiring the affiliate partners that have existing audiences. Affiliate partners without existing audiences will not drive anyone. They will be rounding errors. It will be the long tail where they send you one new customer a year, and it’s more pain to deal with than it’s worth. And you want affiliate partners with large lists, large audiences. Now, whether that’s a big YouTube list, whether that’s a big podcast audience, a big email list, people that are listening to them in one way it’s owned media, right? It’s the channel that they own and they can promote you as an affiliate. 

You have to then go recruit them. If you have a great network, boom, it’s done. Otherwise you’re doing SPR said, it’s basically enterprise sales. It creates another acquisition problem acquiring affiliate partners, a hundred percent on board with this one. Number four, there is no silver bullet. There isn’t one thing that will grow your product from zero to one, but many things will grow it from 0.1 to 0.11. So from point 10 to point 11, if you think about it for the most part, yeah, there’s been a couple silver bullets that I’ve seen, but this is across hundreds, hundreds of companies, maybe thousands where people do stumble into an idea exactly the right time. I had Braden Dennis, the co-founder of fin chat.io on this podcast and them pivoting into the AI space, really was kind of a silver bullet and brought ’em from zero to one, but there’s a bunch of reasons. 

They had a bunch of data that was proprietary for the past several years, and they launched this MVP, I think it was in like four weeks or six weeks. You can go back and listen to the interview. There was a silver bullet there. There was also a silver bullet with Drip, although it wasn’t zero to one, so it’s still in line with what P is saying. But when we launched our visual workflow builder that took Derek five months to build, that was an unlock. And we went from growing from let’s say three to 5,000 MRR each month it went up to 10 KA month. I mean it was noticeable. Noticeable. It really wasn’t unlock, it was very difficult to build. It was complicated, but that feature was holding back a lot of folks from signing up. And so Pierre is right though there are no silver bullets and across the 212 companies that I’m invested in as well as the literally thousands of founders that I’ve spoken with over the years in general, it’s going to be even by the definition of silver bullet that I was giving where it’s not actually a silver bullet, but it’s just a level up or something that really accelerates growth or you feel like isn’t unlock. 

It’s extremely rare, so don’t count on it if you get lucky. We have hard work, luck and skill. Basically what Pierre is saying is develop your skill and work hard. Don’t count on luck, and I would agree with that. Number five, if you don’t know where to begin, copy what works best. That probably means emulating the best in class, not your competitors. Stripe for documentation, Amazon for conversion, apple for copywriting. Expand your copy scope. I really like this advice actually. I dunno that I’ve ever thought of it this way, but he’s exactly right. I know I’ve quoted on this podcast some copy that I’ve seen in Instagram ads that I thought was really clever about things not being the cheapest. These socks are not the cheapest because it’s not cheap to make amazing, awesome socks, and he’s right. Amazon obviously spent a lot of money converting and Apple does have quite good copy and Stripes documentation is amazing. 

So I think this is great advice. Hell, you’ll hear me on this podcast, talk about Picasso, talk about Paul McCartney’s baselines, talk about John Lennon writing Strawberry Fields forever. Talk about Dave ett on his Comic lab podcast. He’ll talk there about drawing comics and the philosophy behind being a self-employed entrepreneur. Basically, as a comics artist, I pull things in from all kinds of disciplines to help me make sense of this B2B SaaS landscape, and I definitely think you should as well. I like this advice a lot. Number six, once you find an acquisition channel that works, forget everything else, every dollar spent elsewhere is a dollar that could have been spent with a guaranteed and increasing return since you’ll get better at this acquisition channel. In general, I agree with this. The only time that I see it, I guess not say not working is when you top it out. 

If you’re doing SEO and you kind of own all the keywords you think you can own or you’re running ads and you’ve topped out all the ads, that’s when you do have to look for something else. But if I have an acquisition channel that is halfway working, much like, look, we started going into YouTube and it kind of worked and then we pumped tremendous amount of time, attention, energy, and dollars into growing our YouTube channel and LinkedIn is the place we’re doing that now. We’ve found that LinkedIn resonates with folks. It’s a lot of you listeners are on there. And so now we are recording a bunch of videos, creating a bunch of carousels for that. And I won’t say we’ve forgotten everything else, but I do like the idea, especially in the early stage of being extremely focused on what’s working and grinding on that for three to six months until you feel and three to six months to kind of get it to a place where it’s working. 

And then depending on the channel, you could then literally spend a year or two just expanding, expanding, expanding and growing that single channel without adding anything else. The only time I think you get in trouble with this is when you have a multimillion dollar company, two, three, $4 million of a RR, and you’re still relying on a single channel. That’s when it makes me nervous because even if it’s SEO, which is huge, man, what if Google accidentally de ranks you or delists you? If you don’t have any other channels, it becomes dangerous, but it’s all about that risk versus reward calculation that you have to do as a founder, as to when should I branch out into the next one? What you don’t want to do is try to experiment with and develop four channels at once because you’re basically probably with your limited resources, not going to succeed at any of them. 

So I definitely like this. Advice number seven is be the generalist hire specialists. The best way to work with people, better than you is to find those who excel at one thing. People who are good at everything will not work for you. They’ll build their own company. Yeah, I mostly agree with this. As a founder, you have to be a generalist hiring specialist, especially in the early days. I think it’s helpful. Well, there’s a couple ways to look at this, right? In the early days of your startup, you often need someone to do two things at once because you don’t have enough support to keep someone busy. You don’t have enough customer success to keep ’em busy full time. But man, if you can hire someone who could do both, would you say they’re a specialist? I don’t know. They’re kind of doing two roles technically, but I wouldn’t call ’em a generalist, so maybe this is in line with what Pierre is saying. 

As a company gets bigger, you definitely hire more specialists. I think people who are good at everything are still hireable. I think people with multiple skill sets, like Tracy Osborne, who’s been on this show many times, she’s an author of multiple books. She’s a graphic designer, she can write copy, she can do build Funnels, email marketing, she can manage people. She runs the accelerator. She and I are doing sales calls currently for SaaS Institute, which is the premium coaching for seven figure SaaS founders, SaaS institute.com, if you’re curious. So she can do a lot of things. And while she has built her own company, she did come on board early with TinySeed because we are doing really interesting things that she wanted to be part of. So there are times when you can paint a vision, paint a picture of what the future will look like, and granted, we did have budget TinySeed raised funding. 

We have currently $42 million under management, and the management fees from that allowed us to hire someone more senior who could do more things. And I think in this case, Pierre is talking to Indie Hackers. She’s not expecting ’em to have funding in the bank to be able to hire someone like a Tracy Osborne. So this is where I’m just adding nuance on a podcast. And again, if I was on Twitter, it would be one sentence and I would leave it behind, but I think that in the early days of a bootstrapped SaaS or a cash strapped SaaS, as I might say, I like to hire people who have that skillset, but maybe who have one other skillset like, oh, they’re in customer support, but then maybe they also can write support docs and maybe they could do blog posts. It’s a stretch, but maybe they could help with some other thing. 

You don’t want to search for a unicorn, someone who’s good at three things. Hiring generalists is really challenging, but I do like the gist of this advice, which is to be the generalist and then usually hire folks who are good at, especially if they’re contractors, actually freelancers or contractors, if I’m working with them, yes, I want them to be extremely specialized. I can just hire a bunch of them for all of the little things that I need done. I don’t need ’em to work part-time. Number eight, never offer a plan with unlimited features. It leaves money on the table for whale customers who could make up 70% of your revenue. And I think Pierre is talking from experience here. I don’t know if he took this one from the tiny C Playbook, which we have a pricing playbook where we talk about this kind of stuff, don’t do unlimited, or if they just discovered it on their own, but a hundred percent no unlimited. 

The only time, I mean, there’s some rare instances where you can offer unlimited something but not your value metric, right? If you’re measuring based on the number of email subscribers, there is no unlimited email subscriber plan with MailChimp or if I was starting an email service provider, you can offer unlimited other thing like, Hey, you get unlimited sends within our terms of service because that’s not the value metric that you are charging based on. And ASPR says, these whale customers are, your large customers are going to make up a huge chunk of your revenue if you do your pricing right. Number nine, if you can’t offer both a cheap plan and exceptional support, then don’t offer a cheap plan feature. Gating support means potential. Big customers will have a terrible experience and look elsewhere, and worse, you’ll never hear from them. And then I’m going to add and worse, everyone at that cheat plan will bitch about you on social media, on Reddit, on private forums. 

It’s not a good look. I agree here, don’t do it. Number 10, there is absolutely no reason to add Google login and any relevant social logins to your signup page. I think I disagree with this. I have seen folks, Ruben Gomez with Sewell and O Heat and Shaw did this where they add the Google login and it does increase their funnel. It increases the number of folks coming through their conversion funnel. So I think that’s the reason to me, there’s no other reason other than to improve your funnel likely. So I’m curious if Pierre and Kevin, his co-founder, have firsthand experience with this one or where it’s coming from because I do think I disagree with him on this one. Number 11, read all your competitors reviews on G two and Capterra several times per year. I love this idea, not only so you get an idea of what people are upset with, and that can help sometimes guide your direction and your positioning and your copy and your strategy and how you do support and all that stuff. 

But it can also help you in sales calls where you can specifically point out to a review or hey, you can say, Hey, go to look at Capterra. Here are the general complaints. I think this is really good advice. Number 12, it’s delusional to think that if you can make it to 10 KMRR, you’ll magically get to 100 KMRR. There’s this little thing called churn. That’s funny. Yeah, I mean, 10 Xing a business like that always requires, it usually requires you to do something different. It doesn’t always, but definitely there’s churn. And oftentimes as you get bigger, you’ll find that there are headwinds that creep up that you just can’t foresee until you get there. And then there’s churn number 12. If you share your success on Twitter, you will get copied 100%. There’s no way around it. He’s probably right. I mean, I’ve shared my success at conferences and on this podcast, and I’m usually copied a hundred percent. 

I think everything I know hit tail a hundred percent was copied almost pixel for pixel Drip was copied by several folks. TinySeed has been copied. MicroConf has been, yeah. All right. He’s right. It’s on Twitter. If you share you’re success anywhere, you’re going to get copied. Yeah, it sucks. It sucks, but it is the way things go. Number 13, people who tell you build this feature and all subscribe will never subscribe to your SaaS. He’s probably right. And in fact, here’s something that we used to do well, I have a couple counter examples, but it’s small numbers, but I remember in the early days of Drip when people would say this, I would say, great, sign up and your credit card. We will pause your billing until this feature is ready and the day this feature is ready, we will unpause your account. And I got some people to do that and it worked, but I’m not saying that to counter this because he’s mostly right. 

There’s a lot of people. What is the one on Comic lab? The co-host, Brad Geiger says the people who tell you, I would buy that comic or that joke, if it was on a t-shirt, we’ll never buy it. And he has all these examples of putting it on a little red bubble t-shirt, sending it to him, and never making a sale and never is a strong word, but realistically, you get the idea. It’s like most people say these things and just don’t mean it. So what I would definitely avoid is hearing build this feature and I’ll subscribe and going off and building it based on just that because the odds are pretty low. They’re actually going to follow through. Number 14, the Mom Test by Rob Fitzpatrick are the best 130 pages you’ll ever read about product development, and I don’t know that I can disagree with that. 

I would add in two other resources, actually deploy Empathy, the book by Michelle Hanson and the market chapter of the SaaS Playbook. I don’t think I would want to write an entire book on product development. It’s something I know how to do, but I don’t feel like I’m a world-class expert at it, but I think I know enough that I could write a chapter about it. I think there’s 30 pages or something in the SaaS playbook, and that’s another resource that I think is maybe not talked about enough out of the SaaS playbook. I think there’s some good guidelines in there. So mom test, deploy empathy and the market chapter of the SaaS Playbook number 14, and there’s only 16, so we just have another couple to go. The easiest way to sell your product when you start from zero is to provide value to your target demographic for free. 

Participate in forums, engage in Facebook groups, answer on Twitter. People will like you want to know more about you and will be open to learning about your thing. It’s not a bad way to go and this way to do it without an audience. Or if you have a network of people with audiences, it’s easy to get on their podcast or get on their YouTube channel or write something for their email newsletter. Whatever form that audience takes, it’s easy for you to get in front of them. Obviously, if you have your own audience, that’s fine, but it’s not something I would spend a ton of time building. I do think that forums Facebook groups, answering things on Twitter and being generally helpful to a demographic is good advice. Number 15, launching on Product Hunt is a nice baptism of fire if you’ve never launched anything, but don’t overthink it. 

It’s not as impactful as it used to be. I would agree with that. And I think even more so today. Again, this was written eight or nine months ago and the 16th and final controversial take, you’re probably never going to sell your SaaS for a 10 x multiple. Heck, you’ll probably never be able to sell your SaaS at all. That doesn’t mean you don’t have a great asset, but two to five X multiple is what happens in real life 99% of the time. And for this one, I think it depends. If he’s truly talking to indie hackers who build small lifestyle businesses, then I think that’s true. And I think when you look at Quiet Lights, numbers or like acquire.com will put stuff out, FE international, these smaller assets where you’re just selling the tech, it’s net profit or seller discretionary earning multiple, but let’s just say net profit multiples are like five to seven, four to seven, five to eight, four to kind of in that range. 

And then if you get to about a million and a half, 2 million a RR and you’re growing and you’re selling not just the technology but kind of the team, like the whole company, the product, everything you’ve built, that’s more than two to five XARR usually. Now I have seen, I saw one that was, what was it? Super flat and it went for 3.5 x. I’ve seen some go in that two to four range, but that could be declining or flat. But if you are growing healthily, I would think, Hey, I might be able to get, it depends on the time. It really does depend on what year you selling, because in 2021, you sell for a lot more, and then in 2025, the multiples were down. But have I seen exits for five to 10 XARR and up more than 10 XARR in the past 18 months for multimillion dollar SaaS companies? 

I have, and I’m intimately, this is not secondhand. This is firsthand knowledge of being affiliated with it. And so this is where it just depends. Multiples are, if you think about a bell curve and there’s the bottom end, which is the, it’s very few sell in that range and the top end, very few sell in that range, and then there’s this big kind of bubble in the middle and on the bottom end, it’s usually declining or flat or your churn is high. Growth is the number one factor. Churn is the number two factor. And man, if you are two, three, 4 million and you’re growing a hundred percent year over year or 50% year over year, you can get crazy high multiples. And then it also depends on just who’s in the market for it, who really wants this? Are you vertical SaaS versus horizontal? There’s a bunch of factors that go into it, so these multiples are helpful, but realize Pierre is probably right. 

You’re probably never going to sell your SaaS for a 10 x multiple, and in fact, you’re probably never sell your SaaS at all. It’s not an unreasonable thing to say. So that’s it for Pierre De Wolfe, co-founder of Scraping Bees, semi controversial takes on X Twitter. I hope you enjoyed walking through those with me. I really enjoyed just thinking through them, asking the what ifs and expanding on them, because again, that’s the beauty of a podcast is that we can sit here and think more deeply about it than you can on Twitter and explore all the ways that these things are true today. Maybe they weren’t true 10 years ago, maybe they won’t be true in 10 years, but at least for now, I think Pierre’s pretty close to being dead on with his takes. Thank you for joining me again for this episode of Startups of the Rest Of Us, the podcast for ambitious B2B SaaS founders. This is Rob Walling, signing off from episode 768.