A few weeks ago, my brother completed high school! His graduation was the culmination of a personal “no-sibling-left-behind” mission that I set to help my siblings attend college. My brother moved in with me “fresh-off-the-boat” right after I graduated from business school. I assumed guardianship of a teenager when most of my friends were setting up their own families. My adult life started in reverse…hence the title. My four year experience with my brother contains parallels to the investor/entrepreneur relationship during an investment cycle. I wanted to share a few lessons:

• NO helicopter parenting – I consistently felt the urge to hold my brother’s hand through tough assignments and difficult personal situations. However, I observed that the more I got directly involved, the slower he progressed and the weaker his resilience became. Additionally, I’ve learned that college admissions reject applications with evidence of adult meddling. Similarly, companies subjected to “helicopter-parenting” from existing investors might scare off potential new investors due to perceived operator incompetence. Also, investor intrusion is often a sign for strategic misalignment. The best role for investors is to facilitate the execution of the company’s vision through supporting competent operators.

• Progressive chaos is good – My brother’s stay was chaotic. At the beginning, the challenges were rudimentary, e.g., confusion about class scheduling, misplaced laptop/phone etc. Over time, the challenges became more complex, e.g., deciding on colleges to apply to or unpacking the emotions of love. Chaos is a constant for businesses, but its nature should evolve similarly. Entrepreneurs that succeed face increasingly complex problems that if cracked, will create sustainable competitive advantages critical to return generation.

• Jack of all trades – About halfway through this journey, I increasingly became overwhelmed and occasionally dropped the ball in other important areas e.g., love, fitness, sleep. I paid the price. Unfortunately, “I took on too much” is not a valid excuse for poor execution. Investors/entrepreneurs must learn to efficiently manage their myriad of responsibilities through tools such as saying NO, clear communication, delegation, humbly seeking help, outsourcing, better time management, etc.

• It takes a village – My brother and I didn’t always get along since we spent too much time together during his “teenage phase”. However, different mentors, at different times, built credibility and ability to influence him on important issues. Companies must surround themselves with a deep bench of trustworthy stakeholders that add value. In times of internal conflict, there needs to be someone who steadfastly remains on the side of value.

• There’s a seat for every a** – At the start of freshmen year, I considered my brother to be Harvard material, but when the college process begun, we had been humbled and were “just happy to be here”. After we rid the anxiety, all stakeholders convened to assess his grades, preferences, goals and curated a list of schools that fit his profile. He got in. Not every startup becomes a unicorn, goes public or is acquired by Google. Stakeholders should explore other avenues of value realization e.g., recaps, partial sales, etc.