CEO OS
Books ·February 24, 2025

The SaaS Playbook

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Highlights

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. — location: 262 ^ref-13868


Subscription revenue is a business cheat code. — location: 399 ^ref-15463


Recurring revenue protects you during recessions and builds on itself every month. Every business wants recurring revenue, but only some can pull it off. — location: 400 ^ref-64454


Most entrepreneurs don’t have enough conversations with potential, current, and past customers. — location: 477 ^ref-52008


There’s another reason entrepreneurs don’t talk to customers: fear—fear that they’re bothering them, fear the customer will say something they don’t want to hear, fear that it’s a waste of time. — location: 480 ^ref-30163


Who should you be talking to? Prospects Customers People who decided not to become customers People who became customers and then canceled — location: 490 ^ref-7143


Asking the Right Questions The key to getting actionable information from customers depends on whether you’re doing early customer discovery or researching how (and whether) to build a new feature. But typical questions might include: Can you walk me through a sample flow? What problem are you trying to solve? What do you currently use to solve this problem? What did you use in the past? What are some of your biggest frustrations about this solution? — location: 494 ^ref-32211


In these conversations, this is the time to put your consultant hat on and have a conversation entirely focused on your customer’s needs, not your product—this part is important. — location: 506 ^ref-2625


Your customers don’t know how to build software as well as you do, and even if they did, they’d never match the insights about the market you’ve learned building your product. — location: 516 ^ref-44925


I wanted to build a product that people used—a lot of people—and that meant learning how to take certain points of feedback to heart and discard the rest. — location: 520 ^ref-11398


As a bootstrapper, time and money are precious, and feature requests can wipe out both quickly. — location: 588 ^ref-6424


For one, a competitive market is proven. You already know that people are willing to pay for the problem your product solves. — location: 595 ^ref-14423


You’re not going to outmuscle or outspend entrenched, well-funded competitors. You need to use their biggest strength (their size) to your advantage. — location: 631 ^ref-45402


unless you’re losing deals to specific competitors on a regular basis, it’s more helpful to keep your eyes on your own paper. — location: 647 ^ref-30144


In SaaS—particularly in bootstrapped SaaS companies—the network effect moat comes not from users, but integrations. — location: 692 ^ref-13630


Having a strong brand means you’re in a lot of conversations. When people discuss options, you’re in the mix. — location: 700 ^ref-13432


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. — location: 715 ^ref-25382


Most APIs are difficult to leave because to do so requires expensive developer time to integrate with a new product. Companies like Stripe, Twilio, and SendGrid have a pretty hefty switching cost moat. — location: 723 ^ref-17831


For example, a social media scheduling tool is easy to switch from because there is no critical history stored or complex workflows that need to be recreated using a new tool. — location: 728 ^ref-41623


If your company isn’t growing, you don’t need to chase a siren song. You need to get to the root of the real problem, one that’s not usually fixed by the approaches discussed below. — location: 745 ^ref-17104


“If no one’s complaining about your price, you’re probably priced too low.” — location: 806 ^ref-14696


When you segment your customers by size and usage, you start to see how your pricing tiers work to offer the most value to customers while driving growth for your business. — location: 818 ^ref-1683


Expansion revenue is when customers pay you more as they get more value from your product. — location: 822 ^ref-51181


Feature Gating. The second way to unlock expansion revenue is by expanding the features your customers can access at higher plans. This tends to be less effective than value metrics because it’s not as intrinsically tied to the growth of your customers’ businesses. — location: 840 ^ref-26714


A loose rule of thumb is to charge 10 to 20 times more than your standard plan. — location: 862 ^ref-22931


Free plans don’t just magically work—you need to understand how they function. — location: 871 ^ref-722


Just remember the golden rule of experimenting: Only change one variable at a time. — location: 936 ^ref-48278


revisiting your pricing every six to 12 months because if you’re like most founders, you’re probably charging too little. — location: 946 ^ref-8824


Dropping your price is rarely the answer when it comes to product-market fit because pricing is such a huge lever in the business. — location: 961 ^ref-13340


When you announce a price increase, use this template: Set the stage for the value your product offers (i.e., we’ve been around for some time, we’ve become a trusted provider in this space, etc.). “We’re changing our pricing.” Let them know up front what’s going on. Provide high-level justification about why you’re changing your pricing (i.e., we’ve added tons more value, we’re in a completely different space than when we launched, we’re expanding our features, etc.). (Optional) Offer more specifics about whom it impacts, when price increases will go into effect, etc. (Optional) Provide more justification if you feel it’s necessary. “Reach out with questions.” Let them know your doors are open for questions, comments, and feedback. — location: 1024 ^ref-6546


the only way to reliably build a business was to get good at marketing. — location: 1059 ^ref-42749


founders need to learn SaaS marketing strategy or risk losing control of and visibility into a crucial part of their business. — location: 1071 ^ref-56122


most markets prefer high-touch. Switching from low- to high-touch was really hard for me because it wasn’t what I wanted, but it’s what propelled us to product-market fit. How you sell is as important as what you sell.”. — location: 1078 ^ref-55348


Higher-touch funnels also tend to focus more on outbound marketing tactics like cold-calling, cold-emailing, and LinkedIn outreach. — location: 1090 ^ref-53953


Keep in mind that you need to have enough traffic coming through your funnel that reliable patterns appear. If you’re only tracking a handful of customers, you won’t have enough data to see noticeable patterns. — location: 1140 ^ref-42014


Do you have a lot of website traffic, but no one is signing up for your trial? You probably have an issue with your value proposition, marketing copy, or positioning. — location: 1146 ^ref-11288


If you’ve built a tool for developers, you can take a look at other tools your audience would likely use. If they’re not direct competitors, contact the founder and ask for a quick call. Say, “I know you market to developers. Could you spend 30 minutes chatting with me about what’s working for you?” — location: 1310 ^ref-5022


But even if you don’t think of yourself as a salesperson, every founder needs to be able to sell—whether you’re talking to potential customers, trying to raise investment, or even just “selling” the company’s vision to new hires. — location: 1355 ^ref-15897


“When selling SaaS, think of yourself as an unpaid expert who’s helping the prospect solve their problem using software.” — location: 1360 ^ref-20052


You’re putting on your consultant hat to help your prospect define their problem and come up with a good solution. — location: 1362 ^ref-3434


Thinking of yourself as an expert problem solver first sets a good tone for sales demos. — location: 1364 ^ref-62653


Asking even a few questions about budget, timeline, and the problem they are trying to solve can be a window into whether it’s worth your time to jump on a demo. — location: 1371 ^ref-64330


What Problem Are You Looking to Solve? Your demo is not a product tour; it’s proof you can solve their problem. Focus on the customer’s pain and how you can fix that. — location: 1386 ^ref-14079


How Big Is Your Organization? Are they a solopreneur with 500 people on their email list? A company with a few dozen employees? A Fortune 1000 company with an intense enterprise sales process? — location: 1397 ^ref-30148


Toward the end of a sales demo, it’s good to get a sense of who else needs to weigh in on this decision. Are you talking to the decision maker? Does your prospect need to go back to a group? Is there any collateral you can provide, like a PDF or a guide, that will help them champion your product to their organization? — location: 1406 ^ref-49517


You need a good process for qualifying prospects before they get to you so you’re not stuck doing demos with people who will pay you $30 a month or are the wrong fit for your product. — location: 1418 ^ref-61558


Hiring someone to help you with sales comes down to whether you’re good at it and whether you enjoy — location: 1431 ^ref-889


Sales demos are usually easy to teach, and as a founder, your energy will be better spent elsewhere. — location: 1434 ^ref-54658


When building your team you should delegate roles, not tasks. — location: 1448 ^ref-36809


In a perfect world, you’ll find that what the company needs most urgently is one of the things you’re not good at or don’t enjoy. — location: 1488 ^ref-5382


focus on building skills in sales and marketing and start hiring developers to get yourself out of the nuts and bolts of the code. — location: 1539 ^ref-48117


As a founder, you will absolutely be on a Manager’s Schedule, which cuts the day into one-hour increments you can fill with all those necessary meetings and other tasks. — location: 1549 ^ref-18883


Because for bootstrappers, a lack of money isn’t what kills businesses. It’s founder burnout. — location: 1570 ^ref-16667


Think of Your Job Description as a Sales Letter. Your job description should convince the person reading it that you have a fantastic company and that they should apply. — location: 1686 ^ref-7123


Bonuses can make people feel left out or that you’re playing favorites. They might feel like you’re giving more money to someone who doesn’t deserve it. — location: 1727 ^ref-10832


Equity is tricky, though. An equity holder only makes money if you sell the business or pull out dividends. — location: 1734 ^ref-58035


Because bootstrapped startups tend to grow more slowly and deliberately, equity isn’t always as much of an incentive. — location: 1736 ^ref-21700


Stock options are the standard startup approach to getting deeper buy-in from employees. An option just means an employee has the option to purchase a share of stock in the company. — location: 1746 ^ref-46368


Consider structuring profit sharing as a pool rather than a committed percentage to an individual. — location: 1758 ^ref-25331


You don’t have to be a metrics savant, though. — location: 1812 ^ref-37691


two most important metrics are MRR and month-over-month growth rate. — location: 1815 ^ref-59582


Tracking the 3 High/3 Low Metrics (six in total) will tell you two important things: How healthy your business is When your revenue is going to plateau These metrics aren’t difficult to track. A dashboard like ProfitWell, ChartMogul, or Baremetrics can connect to your payment processor and give you the data at a glance. — location: 1821 ^ref-46759


Churn is the death of SaaS. I’ve seen multimillion-dollar acquisitions fall apart because of high churn. — location: 1968 ^ref-26904


Once you have decent product-market fit, your churn rate becomes highly relevant because it’s how you know when you’re going to plateau, and it’s part of your LTV calculation, which is one indication of the strength of your business. Reducing churn is a critical part of keeping your business strong. — location: 1979 ^ref-61208


Success comes down to three factors: hard work, luck, and skill. — location: 2092 ^ref-52783


You can control two of these factors: hard work and skill. Although we can attempt to create our own luck, we do that by working hard and acquiring or improving our skills. — location: 2104 ^ref-48364


Skills can be improved through applying hard work to a particular field of study, for example: copywriting, visual design, filmmaking, coding, or SEO. — location: 2106 ^ref-22331


You can also control your mindset. — location: 2109 ^ref-11996


Successful Founders Have a Bias toward Action. When in doubt, they do something. They don’t wait around; they don’t procrastinate. They don’t think of reasons it should take longer—they start shipping. — location: 2111 ^ref-45388


Certainties are things that need to get done, and you know how to do them. — location: 2163 ^ref-21675


Risks are the things you’re not sure of. — location: 2165 ^ref-55652


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. — location: 2233 ^ref-36285


Making the mental shift from “everything will end” to “we’ll switch to plan B, C, or D” has been one of the biggest leaps in my own psychology. — location: 2285 ^ref-63136


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