The SaaS Playbook

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You can also circumvent some of the more painful lessons on your way to developing your founder gut by watching, listening, and learning from others (View Highlight)

One of the best shortcuts in life is finding an expert and apprenticing under them


You might join a Mastermind Group and learn from your peers (View Highlight)

Create or join a mastermind group


I can’t underscore enough that learning from others is a great way to develop your founder gut. You’ll save so much time and heartache than if you insist on making all your own mistakes. (View Highlight)

Where possible, learn from others instead of making your own mistakes


The problem was that I was often ineffective at what I was working on. I could get a lot of things done “efficiently.” But becoming “effective” took a lot of hard work and learning. (View Highlight) - Note: Efficency vs Effectiveness Efficiency vs Effectiveness


Effectiveness is when you do only the two tasks that actually drive your business forward. (View Highlight)


Risky areas require founder-level thinking. Certainties only require the ability to execute them and can be handed off to task- or project-level thinkers. (View Highlight)


As revenue grows, you should begin hiring so you can delegate your certainties. You can hire someone to write code, write a newsletter, or file your taxes (all certainties). You should focus your energy on areas of risk because risks move your business forward, and they require a level of problem-solving that is hard, if not impossible, to hire for at this stage of your business. (View Highlight)

As a founder you should focus on areas of risk


If you’re working nights and weekends, raising enough to fund a year or two of your salary can be a game-changer for your company. Being able to quit your day job and focus full-time makes a night-and-day difference in achieving escape velocity (View Highlight)


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. (View Highlight)


My process for solving problems has moved from stressing about everything that could go wrong to mapping out three or four possible options if things do go wrong. Often these options are not optimal, but none of them would be business-ending. (View Highlight)


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. I’ve realized this over the past few years, but I heard it in full force in the podcast episode I mentioned at the start of this section. (View Highlight)


Masterminds are small groups of people that have similar experiences, challenges, and trajectories in their businesses. Simply put, they embody the phrase: Two (or three) minds are better than one. (View Highlight)

Mastermind Group


My advice: find a mentor or two. But no more. This keeps your information consumption at a reasonable level while allowing input from outside sources. (View Highlight)


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. (View Highlight)


The two biggest things that have helped me in my journey as a founder are masterminds and founder retreats. Without those, I sincerely don’t think I would be as successful as I have been. (View Highlight)


I booked myself a hotel on the coast and drove out for the weekend with no radio, no project, no kids, and no distractions. Over the course of that two-and-a-half-hour drive, things began to settle. I started feeling everything I hadn’t had time to feel for the past year. In the silence, I had sudden realizations because I was finally giving them quiet time to emerge (View Highlight)


If you’re considering a retreat, several years ago Sherry wrote an ebook called The Zen Founder Guide to Founder Retreats that explains exactly what questions to ask yourself, the four steps to ensuring you have a successful retreat, the list of tools she recommends bringing along, and how to translate your insights into action for the next year. (View Highlight)

Founder Retreats