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“It’s easy to criticize from the stands. What’s hard…is doing something.

It’s not just that people like to criticize other people, it’s that they like to criticize other people when they haven’t achieved much themselves.”
Rob Walling
“The genius of niches is they are too small for large competitors, allowing a nimble entrepreneur the breathing room to focus on an underserved audience. Once you’ve succeeded in that niche, you can leverage your success to establish credibility for your business to move into larger markets.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“I know that this sounds sacrilegious to a software developer, but unless you’re marketing to software developers, your order of importance is market, marketing, aesthetic, function.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“There are superpowers to being bootstrapped. One is that you don’t need anyone’s permission to start or build your company. Another is that your business doesn’t die until you quit. Bootstrappers don’t run out of money; they run out of motivation.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“The up-front fear is a big indicator that you’re going to grow as a person if you proceed through it. And, frankly, the terror wears off pretty quickly.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“In your personal life, money saves you hours. In your business, money saves you years.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“White Labeling White labeling is when another company pays you to license your product and present it with its own branding, and the moment you launch a successful product, people will start emailing you with “exciting opportunities” to white label. For the most part, these conversations are a big waste of time. Usually what you have is someone who wants to start a business but can’t build their own product. They want to pay you per account they add, but they have no audience or distribution. In the end, you’ll spend a bunch of time talking to them, writing up contracts, and taking feature requests—for nothing. If you’re approached about white labeling by a large player, it’s worth having the conversation. You know they’re not wasting your time because they don’t want to waste their own. To justify the effort of white labeling, I recommend charging an up-front fee. We’re talking tens of thousands of dollars—$30,000 to $50,000 at a minimum. If someone balks at paying that fee, they’re not willing to put enough skin in the game to warrant your efforts. I’m not a fan of white labeling in most situations. It’s a way to serve customers and make money without building a brand. We discussed above how a brand is a moat, and losing that is an unfortunate consequence of white labeling.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“The sweet spot for your work should be where all three intersect. If you’re focusing solely on things you’re good at that bring you joy, you can get stuck galloping down paths that are detrimental to the needs of your company. If you’re doing things the company needs that bring you joy (but you’re not good at), then you’re dragging your company down. But if you’re stuck doing things the company needs that you’re good at (but don’t like), that leads to burnout. That’s exactly what I was doing. I hired an executive assistant who lightened that load for a bit. She helped streamline a few things and made appointments, but what I really needed was someone to whom I could delegate at another level. At the time, I felt like we couldn’t afford someone who wasn’t contributing to the bottom line of the company. In retrospect, this was one of the biggest mistakes I made while building the company. I should have hired someone who could come into the office and handle operations. Things like legal, payroll, HR, and facilities. Most of these were outsourced to external providers, and it was just a matter of interfacing with them. As I look back at my descent into burnout, one thing that could have saved me was having enough funding to hire someone to do the work that didn’t bring me joy. Or prioritizing spending money on hiring and delegating tasks that didn’t move the business forward but were contributing to my lack of satisfaction at work. I hope you’re not at a place where the next section is helpful to you. I hope that you’re smarter than I was and are putting measures into place to keep yourself from burning out like I did. As Jason said in his talk: “The right question is what should you be doing differently now […] in order to build a company that’s more healthy and prosperous, and also avoid this balloon payment of emotional toil at the end.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“Generally speaking, the lower your product’s price point, the higher your churn. Some of the TinySeed companies that cater to hobbyists or very small businesses have churn in the 5% range, and while I’d love to see churn lower than that, it’s okay because they are in massive markets and have a very low cost to acquire new customers. For most companies like the type we’re discussing in this book, I suggest shooting for gross revenue churn as low as possible, certainly under 3% per month. At the venture scale, successful companies have less than 1% gross churn.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“It’s Taking Customers Too Long to Find Value. If customers aren’t seeing value in your product, it could be a matter of education. The standard approaches are to send onboarding emails to orient them to your product (see Val Geisler’s Dinner Party Strategy) and to hire a customer success manager to walk new accounts through the onboarding process (assuming their price point makes this worthwhile). When you have a high price point, hiring someone to help with onboarding can go a long way toward helping your customer find value. Essentially, you’re trying to help new customers find your minimum path to awesome (MPA). Basically, the moment when everything clicks and your customer says, “This is amazing!” For a social media scheduling app, maybe it’s when they load the first few posts and realize they can sit back and let your product take care of the rest. For an email product, it could be the minute they get a form installed on their website and start seeing new subscribers. It’s not always easy to find the MPA. Your product might be so complicated that there are many paths to seeing value. In that case, the burden is on you to educate your customers about how to get the most value in the shortest amount of time. One way to shortcut the process is to interview customers who are actively using the product and ask them when they first realized how your product would help them. With Drip, we even built a custom internal dashboard to track where trial users were along the path to awesome. Had they created their first email list? Installed a form on their site? Activated that form? I could watch individuals or groups of users go through those steps during the trial phase and see a leading indicator of how many were likely to convert into paying customers.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“As a self-funded startup you want a market that is already looking for your product, even if it doesn’t exist.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“Product Last. Marketing First.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“Owned Traffic Channels A friend of mine owns a SaaS company that’s competing in a massively crowded space. His product gets 500,000 unique visitors a month because he’s exceptional at search engine optimization (SEO), and his company ranks on the first page of Google for many high-volume terms. He owns these organic traffic channels in his market, so even though other names on those pages might be more recognizable, he can stay highly competitive. Even if you own a high-traffic search term on Google, Amazon, or the WordPress plugin store, you can have a pretty commoditized product that can still succeed. One caveat is that this moat can be a bit dicey to maintain because the algorithms at any of those companies can change quickly—and have. Google’s many updates have tanked businesses overnight that depended solely on SEO-driven traffic.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“The lesson here is that the narrower you can make your product while still maintaining a large enough market, the more profit you will generate. It’s that simple – if you can find a small group of people and make them amazingly happy, you will make money.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“Content Marketing. Although it is often coupled with SEO, content marketing relies solely on virality or on building an audience slowly over time, without the long-term benefit of organic search. This includes writing blog posts you hope will make it to the top of social news sites like Hacker News and Reddit and building a media brand alongside your product (something I recommend only for very well-funded companies). It also includes producing content to educate people at different steps in their funnel whom you already have permission to contact. Most people think of blog posts when you mention content marketing. However, content can include books, ebooks, audio (think podcasts), video (think YouTube), or even in-person courses that are given away to bring links, traffic, and leads and build credibility. Most founders start by producing the content themselves, then hire people to help with production later.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“This is by far the most common mistake I’ve seen – building something no one wants.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“Don’t Invent Job Titles I used to make up job titles because, as a bootstrapper, I didn’t particularly care what someone’s title was. I didn’t want it to matter—but it really does. When we realized we needed an architect to scale our infrastructure at Drip, we asked our internal recruiter to hire for the job of “Senior Scaling Architect.” She eventually talked us into the title of “Senior Architect.” Why? Because when she ran the data, she couldn’t find enough salary information on the title we’d given her. Not only that, but if we’d used a made-up job title, qualified candidates wouldn’t have known what we were hiring for. There are standard SaaS job titles. Use them. Your ideal candidates have saved job searches for things like “Engineer,” “Customer Service Lead,” and, yes, “Senior Architect.” Ignoring that makes it harder to connect with people searching for the job you’re hiring for. It also does a disservice to whomever you end up hiring. They’ll have a much tougher time explaining their qualifications to their next employer when their job title was “Code Wizard” rather than “Senior Engineer.” Although a treatise on organizational structure is beyond the scope of this book, here’s a typical hierarchy of engineering titles (in descending order of authority) that can be easily translated into other departments: Chief Technical Officer VP of Engineering Director of Engineering Manager of Engineering Senior Software Engineer Software Engineer Junior Software Engineer Entry-Level Software Engineer Note: These titles assume the typical path is to move into management, which doesn’t have to be the case. Individual contributor titles above Senior exist, such as Principal Engineer and Distinguished Engineer. But for the sake of simplicity, I’m laying out the above hierarchy, which will work for companies well into the millions of ARR. Another note on titles: be careful with handing out elevated job titles to early employees. One company I know named their first customer service person “Head of Customer Success.” When they inevitably grew and added more customer service people, they didn’t want him managing them and ended up in a tough situation. Should they demote him and have him leave? Or come up with an even more elevated title for the real manager?”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“There are many ways to ask customers why they churn. At Drip, any customer that canceled their account received an automated email within ten minutes of canceling. It said, “Hello, I’m one of the founders of Drip, and I’d love to hear why you decided to cancel your account.” We got a wide range of responses. Some people would tell us they were shutting their business down—which isn’t something we could fix. Others would say they switched to a cheaper tool because they didn’t need our more powerful product. Others switched to a competitor because they needed a feature we didn’t have.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“When reading blogs or books or listening to podcasts or audio books, take action notes.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“unless you’re marketing to software developers, your order of importance is market, marketing, aesthetic, function.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“Adding Other Verticals Too Early Adding other verticals is the easiest siren song for me to justify. Sometimes it makes sense to pivot or expand to other niches. For example, if you have a product that’s working well for wedding photographers, chances are it will also serve wedding videographers. But unless you’re pivoting your product, you must be extremely careful about adding new markets. For example, if you add wedding coordinators to your wedding photography SaaS, you’re probably dealing with audiences that have different needs—even though they’re in the same industry. The danger of adding other verticals flippantly is that it can lead to a lot of complexity in your product. Unless you already dominate a particular niche and are moving into another or are making a full-blown pivot into the new space, be careful with this one.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“Getting through Burnout I’ve heard burnout manifests itself differently in different people, but for me it felt like a mix of depression and frustration. Not the kind you can clear up with a weekend away, but a long-term, deep sense of tiredness, lack of motivation, and feeling just a little pissed off at all times. This led to my aforementioned stints of staring at Trello for hours and a lack of presence at home. I would be home with the family, but most of the time my mind was elsewhere. I tell this as a cautionary tale: if you find yourself listless, unmotivated, or constantly frustrated as you endure the stress of building your company, it’s unlikely to fix itself. The best remedy for burnout is significantly changing your habits and patterns related to work, including stepping away for weeks, which feels like the last thing you can do when everything is going crazy (whether it’s good crazy or bad crazy). If you find yourself in this situation, you need to address it, or it will get worse. If unaddressed, burnout can lead to terrible outcomes, including long-term damage to your brain. If burnout is a situation you find yourself in, consider reaching out to a professional who works with founders on the mental game of entrepreneurship. Dr. Sherry Walling is one (she happens to be my wife, and she knows her stuff), but there are many other executive coaches and therapists who work with high-performing individuals to manage stress, burnout, and everything else that comes with our line of work. I’ve only started to touch on burnout here, but for an entire chapter about it, check out my third book: The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“Demonstrate How Your Tool Solves the Problem Thinking of yourself as a problem solver first helps solve another common issue I see with sales demos. Instead of giving prospects a painfully detailed explanation of every feature, only show them the relevant parts. Software demos are not tours of your product. You don’t need to take a deep dive into all your settings and obscure integrations, no matter how proud you are of them. Instead, think of a sales demo less as a presentation and more as a conversation. You should be asking questions and listening more than talking. For more on sales demos, I recommend the book Product Demos That Sell: How to Deliver Winning SaaS Demos by Steli Efti.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“Don’t Torch Your Cap Table Your capitalization table is a list of who owns what percentage of your company. Literally: Rodrigo owns 70%, Janine owns 20%, and Fred owns 10%. Your cap table can get complicated if you start taking multiple rounds of investment. I’ve seen cap tables with 40 entries, where the founder still owns 50% of the company, a bunch of angel investors own 5% each, and early employees each own 1% to 2%. A complicated cap table isn’t a deal breaker. But you can torch your cap table if you let early investors or founders take too much of the company. We’ve had multiple companies we’ve been unable to fund because of their cap table. One was a company where the founder only owned 30% because he’d given up 70% to an agency he was working with in the early days. Another founder gave 60% of her company to an early investor who had only invested $50,000. When you let early investors take too much, you end up shooting your business in the foot by making it uninvestable. You also put the majority of the profits into someone else’s pocket. You can also torch your cap table by not vesting founder equity. If you start a company with two other people and split it equally, but six months later one of your cofounders gets a full-time job and leaves, they still own 33% of your company. You and your remaining cofounder are stuck working the next five or 10 years growing a company and putting money in your ex-cofounder’s pocket. This also creates a problem if you want to raise money. Normally in first-round funding, investors want to make sure the founders who are actively working on the business own 80% to 90% of it. This can be fixed with vesting, where you get zero shares during the first year you work at the company and 25% of shares after the first year, then the rest drip out over the next three years. Those numbers can vary—you might decide to say it’s three years to vest. Just make sure to talk to a lawyer when you set it up.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“Either way, you’d have a really good shot at making something that they can’t live without simply because of your intimate knowledge of their interests. And odds are, since your product would be so laser focused to their interests, it wouldn’t already exist.”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup
“Follow Up It’s amazing how many salespeople don’t bother following up. People are busy, and following up until someone tells you they are no longer interested is the process that good salespeople follow.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“One way to make yourself less vulnerable to copycats is to build a moat around your business. How Can I Build a Moat? As you scale your company, you need to think about how to proactively defend against competition. The more success you have, the more your competitors will grab their battering ram and start storming the castle. In medieval times, you’d dig a moat to keep enemy armies from getting anywhere near your castle. In business, you think about your economic moat. The idea of an economic moat was popularized by the business magnate and investor Warren Buffett. It refers to a company’s distinct advantage over its competitors, which allows it to protect its market share and profitability. This is hugely important in a competitive space because it’s easy to become commoditized if you don’t have some type of differentiation. In SaaS, I’ve seen four types of moats. Integrations (Network Effect) Network effect is when the value of a product or service increases because of the number of users in the network. A network of one telephone isn’t useful. Add a second telephone, and you can call each other. But add a hundred telephones, and the network is suddenly quite valuable. Network effects are fantastic moats. Think about eBay or Craigs-list, which have huge amounts of sellers and buyers already on their platforms. It’s difficult to compete with them because everyone’s already there. In SaaS—particularly in bootstrapped SaaS companies—the network effect moat comes not from users, but integrations. Zapier is the prototypical example of this. It’s a juggernaut, and not only because it’s integrated with over 3,000 apps. It has widened its moat with nonpublic API integrations, meaning that if you want to compete with it, you have to go to that other company and get their internal development team to build an API for you. That’s a huge hill to climb if you want to launch a Zapier competitor. Every integration a customer activates in your product, especially if it puts more of their data into your database, is another reason for them not to switch to a competitor. A Strong Brand When we talk about your brand, we’re not talking about your color scheme or logo. Your brand is your reputation—it’s what people say about your company when you’re not around.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“LOW: Churn Churn is the percentage of people canceling their subscription each month, and it’s the Achilles heel that kills (or plateaus) SaaS apps. If you can keep churn low, growth is much easier. If churn is high, it’s a force that’s very hard to outrun. Focus on revenue churn. To calculate this, divide the gross MRR that canceled in a given month by the starting MRR for that month: As a general rule, for most bootstrapped B2B SaaS businesses: Gross churn > 10% = Catastrophic Gross churn 8–10% = Not Good Gross churn 6–7% = Meh Gross churn 4–5% = Fine Gross churn 2–3% = Good Gross churn < 2% = Great With this caveat: if you are focused on high-priced contracts, say, above $25,000, your churn should be lower than the chart above. In that case, I’d categorize fine churn as 2–3%, good churn as 1–2%, and great churn at or below 1%. Churn is such a critical metric because it helps you calculate when revenue will plateau. At some point, the number of new customers you acquire will equal the number of customers you churn out each month. This causes your growth rate to effectively hit zero. You’ve hit your maximum number of customers (and revenue) that you can achieve without changing something in the business.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“raising funding also has the potential to save you years. As Craig Hewett, the founder of Castos, told me, funding allows you to “live in the future” by making investments you otherwise would have had to wait for. When Craig Hewett raised money for Castos, he spent it on hiring senior sales and development team members rather than the juniors many startups are forced to hire because of a lack of cash. This allowed Castos to make progress fast. Ruben Gamez, the founder of SignWell, used funding to invest in compliance (SOC2 Type 2 and HIPAA). They would have done so eventually, but they wouldn’t have been able to afford it until later. This investment allowed them to start closing major deals sooner and grow faster. Strategic hiring can be another way to spend funds. Jordan Gal, the founder of Rally, hired a chief of staff almost from day one. He told me, “Money allows you to hire in such a way that you, as the founder, can focus on whatever your superpower is, with far fewer distractions than when bootstrapped.” Derrick Reimer of SavvyCal burst into a crowded scheduling space by investing funds into SEO and marketing earlier than he would have been able to if he was purely bootstrapped. This potentially shaved a year or more off his marketing efforts. Those are just a few of the ways funding can help when applied strategically.”
Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital
“A study at Dominican University3 revealed that the following 3 factors substantially increased someone’s chance of following through on their goals: 1. Written Goals – “Those who wrote their goals accomplished significantly more than those who did not write their goals.” 2. Public Commitment – “…those who sent their commitments to a friend accomplished significantly more than those who wrote action commitments or did not write their goals.” 3. Accountability – “…those who sent weekly progress reports to their friend accomplished significantly more than those who had unwritten goals…”
Rob Walling, Start Small, Stay Small: A Developer's Guide to Launching a Startup

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