Lost and Founder: A Painfully Honest Field Guide to the Startup World

"Recruit technical leadership with a teaching orientation. The best way to ensure that your CTO is going to make you a better CEO is to hire a CTO who likes to teach. Make it clear that you’re looking for someone to drive change and educate you and the team. Beware CTOs who try to “shield” you from the details. Being able to explain complex things simply is a job requirement."

"Unless what you love is managing people, handling crises, delegating, holding people responsible, recruiting, setting, then constantly amplifying and repeating the company’s mission, vision, strategy, and values, being a startup CEO may not provide you with the work you love to do."

"Promotional pricing, especially when offered to a very large audience, creates an impression that discounts and special offers are part of a brand’s ethos, and that rather than signing up at full price, you, as a potential buyer, should wait until the next promotion launches."

"Underlying this problem is a belief that anyone can be a people manager, and that unlike any other specialized role (e.g., accounting, marketing, engineering, design, or sales), all it takes is the will to manage and an understanding of the problem space. This is bullshit."

"Pro Tip: If you have any type of subscription or recurring revenue, make sure you measure LTV (Lifetime Value—the total revenue customers spend during their relationship with your firm) by referral source(s) and by the number of visits prior to conversion."

"There are two traits fundamental to an effective product-focused business. The first is reach (i.e., the ability to influence a large audience). The second is scalability (i.e., an aptitude for growing revenue far more quickly than costs)."

"She outlines one of the most important things to remember when it comes to transparency: you need to balance it with empathy. If I tell you I hate your haircut, I’m being transparent. I’m also being an asshole."