My Year In Review: Lessons To Make 2024 Your Best Year Yet

Greg Eisenberg, founder of the holding company Late Checkout, recorded a raw, no-holds-barred year-in-review for 2023. He got married, bought half of a business that is on track to generate $2–3 million in free cash flow in 2024, and turned down a $30 million private equity offer. But the episode is not a victory lap. It is a detailed, self-critical autopsy of what worked, what backfired, and what he plans to do differently. The central thesis is that entrepreneurship is a game of a few high-leverage ideas, and that the most important discipline is staying true to your own thesis rather than following conventional wisdom or fear-based advice.

The Cost of Listening to Fear

Eisenberg’s biggest regret of 2023 was taking bad advice. Early in the year, someone told him to keep his innovation agency team lean because a recession was coming and Fortune 500 clients would cut budgets. It sounded logical—tech companies were laying people off, and the news was full of recession warnings. So he held back on hiring. The problem was that the advice was wrong for his specific business. His agency helps large companies build new products and community features, and in a tough market, those companies need new revenue drivers even more. The result: his team was fully utilized all year, and he estimates they left at least $3 million in revenue on the table. “We led with fear instead of lead