Don't Do That: Don't Use Hope as a Strategy

On this episode of Don’t Do That, Kelly Waltrich sits down with Sean O’Toole, founder of 1776ing and CEO of 1776 Wealth, for a conversation about private markets, AI, and why action beats wishful thinking. Sean went to college on an ROTC scholarship and earned a degree in civil engineering. Four years with the 82nd Airborne at Fort Bragg changed his path. He wanted freedom to build his own way, so he turned down engineering offers and started as a rookie broker at Merrill Lynch. His first years in the business included the Long-Term Capital Management collapse, Y2K panic, and the dot-com crash. He later moved to UBS just ahead of the financial crisis, eventually started his own RIA, 1776 Wealth, and ran a private equity business that grew into 1776ing, an infrastructure platform that helps RIAs access private markets for their clients and helps sponsors find capital. During the episode, Kelly and Sean dig into the alternatives landscape. Sean explains why he believes wealth is made in private markets and preserved in public ones, shares his concern that the industry is crushing the J curve by selling easy liquidity, and breaks down how fee layers in funds of funds and continuation vehicles eat into returns. He walks through 1776ing’s white-label model, which keeps each sponsor’s brand front and center, and explains why 80-page decks and crowded data rooms don’t work for advisors and their clients. The two also talk AI, including Sean’s view that AI makes the wisdom of experienced professionals more valuable than ever. Sean’s “don’t do that”: don’t use hope as a strategy. He learned the lesson in the military and says hoping led to nearly all of his failures. He shares how he pictures himself weeks or months in the future, looks back with hindsight, and asks what he can do today instead of waiting for a deal, a market, or a phone call to pave the way. 00:19 – Meet Sean O’Toole 01:29 – From civil engineering and ROTC to the 82nd Airborne 02:48 – Trading engineering offers for a rookie broker seat at Merrill Lynch 04:02 – A volatile start: Long-Term Capital, Y2K, and the dot-com crash 06:56 – Launching an RIA and the private equity business behind 1776ing 08:17 – Adam Smith, The Wealth of Nations, and the story behind the name 11:59 – How Sean sees the alts landscape and where 1776ing fits 17:01 – Why 1776ing runs behind its clients’ brands 19:15 – The J curve and the push for daily and quarterly liquidity 29:11 – How AI makes experienced professionals more valuable 33:17 – Why the “supermarkets of alts” strip away a sponsor’s brand 38:09 – Money-raising businesses versus money-making businesses 41:28 – Sean’s don’t do that: don’t use hope as a strategy 45:27 – Using future hindsight to take action today  Connect with Kelly Waltrich: - LinkedIn: Kelly Waltrich - LinkedIn: Intention.ly - Instagram: Intention.ly Connect with Sean O’Toole: - LinkedIn: Sean O'Toole - 1776ing - 1776 Wealth About Our Guest: Sean O’Toole Founder and CEO, 1776ing and 1776 Wealth Sean O’Toole is the Founder and CEO of 1776ing and CEO of 1776 Wealth. As an engineering graduate of Worcester Polytechnic Institute, Sean later served as an officer in the U.S. Army’s 82nd Airborne Division before spending 20+ years in wealth management with Merrill Lynch and UBS. In 2017, he co-founded 1776 Wealth, an SEC-registered investment advisory firm. As technology began reshaping private markets, Sean saw an opportunity to make private placements easier to discover, diligence, and invest in, not by going around advisors but by equipping them. In 2019, that vision became 1776ing, a technology and implementation company supporting issuers, broker-dealers, and advisors bring private market opportunities to more investors. Why the name? 1776 was the year Adam Smith published *The Wealth of Nations*. Philosophically, 1776ing is a verb: taking action to create one’s own wealth and prosperity.  📩 Stay Informed – Join Our Newsletter! Stay ahead of industry trends and get exclusive updates straight to your inbox: Sign Up Now https://intention.ly/ 💬 Let’s Talk! Have questions or ready to start your next marketing campaign? Contact us: https://intention.ly/contact-us/