• my rating: 3/5
• Most of the advice is common sense or better covered elsewhere. Matt is pretty vocal about this though. He openly says that his while “system” is based on a few standard books he read like Andy Grove’s High Output Management or Getting Things Done by David Allen. So if you’ve read those books, you won’t find much new here. Also given that Matt has worked with tons of incredible companies, there were very little first-hand stories that back up what he’s saying.

Main Takeaways

• Keep your team as small as possible (<6 people) until you have product-market-fit (usually $1M in yearly revenue). Smaller teams thrive in chaos and are ready to tackle new challenges.
• A co-founder’s purpose is primarily to help achieve product-market fit; they may not provide value beyond that point.
• Embrace “Getting Things Done” method by quickly processing tasks, categorizing them, and acting accordingly.
• Batching tasks can lead to more actual productivity instead of constantly reacting to problems.
• Focusing on the positives and having fun promotes better performance and mental well-being.
• Networking should involve specific appreciations and follow-ups to create strong connections. Dedicate one hour per week tofollow-ups and outreach.
• Embrace sales as a crucial component for gaining trust and overcoming technical hurdles in B2B software businesses.
• Establish and maintain impeccable agreements to prevent unproductiveness and decreased morale. A lot of startups suffer because of sloppy agreements. Broken agreements must have consequences.
• Good company culture involves goal tracking, receiving/giving feedback, and creating fun.
• Prevent workplace politicking by having clear written policies about compensation, raises, and promotions.
• Document all processes and tasks within a company wiki to ensure consistency and shared knowledge.
• When hiring new managers, maintain existing processes for a period before allowing changes to be made.
• Assign one person to be responsible for each task to avoid the tragedy of the commons.

On Co-Founders

“Your partner’s purpose is not to be value-add forever. As your company grows, you will likely find people with far greater skills whom you will hire. That’s okay. Your co-founder’s purpose is to help you achieve success in your march to product-market fit. Once you get there and begin the blitzscaling process, be pleased if they continue to add value beyond that point.”

On Hiring

“Y Combinator has another strong belief: founding teams should never grow beyond six until there is true product-market fit. Product-market fit (PMF) is the milestone of having created a product that customers are finding so much value in that they are willing to both buy it (after their test phase) and recommend it. Metrics that show whether PMF has been achieved include revenue, renewal rates, and Net Promoter Score.”

“By contrast, with six or fewer people, the environment feels like a team in battle. Chaos is expected. So when chaos is actually encountered, the team meets it with glee. People who join small teams crave the challenge of new things. They want things to be hard.”

“Finding joy in career development, making that key hire, and putting structures in place so that people love their jobs—these are all things that you must learn to revel in and love. And this will take time, but if your heart’s in it, it’s all achievable. And if your heart’s not in it, think about hiring another CEO.”

On Getting-Thins-Done

“Getting Things Done: The Art of Stress-Free Productivity by David Allen. While the book is dense, it is definitely worth reading in its entirety. The essence of Allen’s system is this: Each day, process every single item in your inbox (defined broadly as all inboxes [email, Slack, text] and all to-dos). If the action takes less than two minutes to complete, do it immediately. If not, then write down what the required action is, and place it on one of the following lists: • Next Actions: These are the next tasks on your priority list separated into areas of context. ○ Computer (actions for which you need access to your computer) ○ Calls (phone calls that can be completed when you don’t have access to a computer, e.g., when riding in a car) ○ Outside (actions that can only be completed outside, such as errands) ○ Home (actions that can only be completed at home) Tasks should be written as single actions (as opposed to broad goals). The key is to not have to think about what needs to be done again once the next action has been written down. The next action should be written so clearly that all you need to do is follow its direction when you read it next.”

On Batching Tasks

“Inefficient leaders waste a lot of time reaching out about or responding to one-off issues in real time. A much more efficient method is to batch your issues and discuss them all at once. This does not apply for urgent issues. Those need to be addressed immediately. But by addressing many issues on a regular basis, urgent issues will soon disappear. To do this, create and use an Agenda list. This is your list of regular meetings. When you think of something that you want to discuss with someone whom you meet with regularly, write it down on your Agenda list. Then, when you meet with that person, check your Agenda list and review everything accumulated there.”

On The Importance of Fun

“It turns out that we perform our best when we are having fun and feeling good about ourselves. If you want proof of this, go to any kids’ sports event where you know the names of the kids. Start cheering positively for the team that is losing, with specific compliments to specific kids: “Great pass, Jimmy.” “Way to be in position, George.” When a kid takes a shot but misses: “Good idea, Joey, it was the right thing to do.” Within five to ten minutes, the tide of the game will start to change toward the team that you are giving specific compliments to.”

“So how do we take advantage of this knowledge to generate a good feeling in ourselves? We ask the right question: “What is good about this situation?” “What is good about this team member?” “What is good about my company?” “What is good about my life?” Or we simply fill in the overarching statement “I am grateful for ____.” Be as specific as possible: names of people, actions they did, and so on. I recommend making this a daily practice. I do it first thing every morning.”

On Networking

“In a First Round Review article titled “How to Become Insanely Well-Connected,” Chris Fralic of First Round Capital says that he reserves one hour each week for follow-ups and outreach, most of which include appreciations. I recommend that you do the same.”

“Just as with gratitude, giving appreciation should be as specific as possible, as in this example: “John, I appreciate you for writing down our sales process and adding it to the wiki. Thank you.” And when receiving appreciation, there is only one correct response: “Thank you.” Do not feign humility by downplaying the act with statements like “It was nothing, anyone could have done it.” No. The person is trying to make you feel appreciated. Anything other than “thank you” will rob them of their goal.”

On Operating in Your Zone Of Genius

“What is the Zone of Genius? Well, there are four zones: Zone of Incompetence Zone of Competence Zone of Excellence Zone of Genius Tasks in the Zone of Incompetence are the things that other people probably do better than you (e.g., fix your car), and therefore you should outsource if they don’t give you joy. Tasks in the Zone of Competence are the things that you do just fine, but others are as good as you (e.g., clean your bathroom), and therefore you should outsource if they don’t give you joy.”

“Tasks in the Zone of Excellence are the things that you are excellent at (i.e., better than others) but don’t love doing. This is the danger zone. Many people will want you to keep doing these things (because they gain significant value from you doing them), but this is the area that you should also look to move away from. This is the hard one! Finally, tasks in the Zone of Genius are the things that you are uniquely good at in the world and that you love to do (so much so that time and space seem to disappear when you do them). This is where you can add most value to the world and yourself. This is where you should be driving toward spending most, if not all, of your time.”

On The Importance of Sales

“In the world of B2B software, sales and customer success will be core aspects of your business. Personally, I’ve never been a natural salesperson. Indeed, in the past I mostly saw sales as a sign of inefficiency. For someone with an engineering mind-set, verbal communication is lossy and has high latency. Add to that the commission that the average sales rep requires and the bro culture that often accompanies the role, and one starts wishing it could be automated away. And that’s exactly what I tried at first. I kept the sales team at an absolute minimum and automated as much as possible to try to make self-service work. But what I found was that at about $2 million in annual recurring revenue, our growth rate flattened out. So what went wrong? It turns out I had seriously underestimated two things: sales is critical to gaining trust, and customer success is critical to overcoming technical hurdles.”

“Since businesses are more price insensitive, it makes sense to raise the price of your product to, say, $20,000 a year. But now you have a trust problem. Enter a competent sales rep. They will smooth the way during the sales process. They will find the key decision maker, make sure that person is listened to, and build trust. They will make promises about the functions of your product, and your customer will always have someone to yell at if things go south.”

“If your company is like 99 percent of SaaS businesses, you’ll find that self-service doesn’t work. If we had relied on it, our revenue would have flattened and never recovered. As soon as we added a sales team, our revenue rocketed. Sales might not be the most efficient thing in the world, but it works. And it will continue to work as long as humans are the ones doing the buying.”

“Don’t just respect sales, embrace it.”

On Sleep

“When you do wake during the night, don’t fight it. Allow yourself to do productive work. If you aren’t motivated to do productive work, do something soothing, like reading from a paper book. Avoid doing something unproductive and stimulating (e.g., viewing social media on a screen).”

On Efficient Communication Habits

“When two people are discussing an issue, the need to be efficient is important. When a team is discussing an issue, the need to be efficient is paramount because each inefficient minute is multiplied by the number of people in the discussion.”

“Reserve the first fifteen minutes of the meeting for all participants to write out their updates and issues. Then use another ten minutes of the meeting for all participants to read one another’s updates and issues. Then discuss and decide. Use this method for two to three meetings, then…”

“The write-up should include both a detailed description of the issue and the proposed solution. Someone may say, “I don’t know the answer.” It doesn’t matter. They should take a guess. Even if they have only 10 percent confidence that their answer is a good one. And they should phrase the proposed solution in very bold, directive terms (e.g., “Do this…”). This may seem aggressive but creates a flag in the sand that generates a much more productive discussion and a quicker decision time, which ultimately is more important than appearing to be humble.”

On the Dangers of Sloppy Agreements

“A very common cause of inefficiency in startups is sloppy agreements. People don’t show up to meetings on time, and they don’t complete the goals that they declare (or they don’t declare goals at all). The result is a spreading virus of unproductiveness and decreased morale. The antidote for this is simple: impeccable agreements. These are (a) precisely defined and (b) fully agreed to (which almost always means written) by all relevant people.”

“There must be consequences for breaking agreements. Implementing these consequences is a two-part process. The first time someone doesn’t meet an agreement, you point it out to them immediately. If they apologize, you respond that apologies are not needed, and all that is required is that they only make agreements that they can commit to and that they meet all the agreements they make, whether by adherence or by prompt communication that they need to alter the agreement. If the person continues to fail at these, there is only one consequence that makes sense: they can no longer be part of the company.”

On Culture

“Your litmus test is whether your team members are hanging out with you and one another outside of work. If yes, you are likely creating good culture.”

“If you are creating and tracking goals, habits, agreements, and key performance indicators (see chapter 23); openly receiving and providing feedback (see chapter 27); and creating fun, then people will be naturally motivated to work hard. They’ll see where the company is going, how it’s moving forward, and how their efforts and their team members’ efforts are contributing. They’ll know that they are heard, and they’ll be having fun.”

On Salary Negotiations

“It often begins very innocently: “Excuse me, can I please talk to you about a raise? I have been at this company for a year now and have shown utter dedication by doing such-and-such, and I believe that I now deserve a raise…” This sounds compelling, and you, of course, want to reward dedication. But if you give a raise based on this conversation, then the whole company will learn that the way to get a raise is to simply ask you for it. Suddenly everyone will be trying to curry your favor. Be very careful here. You may enjoy this behavior, but it is toxic for the company.”

“The only way to prevent politics is to never allow lobbying to be successful, and the only way to do this is to have a written policy about as many situations as possible, particularly around compensation, raises, and promotions.”

On the Importance of Documentation

“After creating a wiki, the question then becomes, “What should we document?” And here is the painful answer: “Everything.””

“Whenever you find yourself doing something twice, write down exactly what it is that you did. If you’ve done something twice, you’re likely to need to do it again, and someone else may need to do it too. When it’s documented, there are clear instructions to follow, which allow for consistency across employees and client situations. Place these written processes in the company wiki. Require that all members of the team also follow this practice to share their knowledge.”

On Dangers of New Managers

““We have noticed that whenever we hire a new manager, they want to instantly bring in their own processes. But then we lose all of our hard-won institutional knowledge that led to the creation of our original process. So we now require that all managers use the existing Bolt processes for at least three months before making any changes. After they know our system in this way, they are free to make the changes they want to. And yet most make relatively minor changes after that.””

On Why Only One Person Should Be in Charge of Each Task

““Tragedy of the commons.” When several people share responsibility for an action or process, often that action doesn’t get done well or at all.”

“Create a document that lists all of the company’s functions and, for each, the directly responsible individual. This is the AOR list. It serves as a routing layer for any questions and ensures that no functions fall through the cracks.”

On Asking for Feedback

“When asking for feedback about himself as a manager, Lachy Groom of Stripe asks, “What feedback are you afraid to give because you think it might hurt my feelings? Please tell me that.””