The Altogether Show with Eric Satz

Shane Mac is particularly proud of one of the several successful companies he co-founded in the last 10 years: Squared Away. Co-founded with his former assistant without venture funding, Squared Away connects military spouses with quality remote employment opportunities.  In addition to Squared Away, Shane is the co-founder and President of XMTP, founder and General Partner of Logos Labs, and a passionate writer and musician. He also co-founded and served as CEO of Assist, which was acquired by Verint after merging with Conversocial. In this episode, Shane provides insight into his impressive trajectory, beginning with crucial advice he received from his brother during his senior year of high school. He discusses the additional influential figures who have helped shape his path and what they have accomplished together by embracing curiosity and communication. Shane opens up about managing anxiety and sobriety while discussing relocating from San Francisco to Nashville, and his exciting ideas for the “switchboard” city. Later in the episode, Shane talks Eric through his current projects, including a glimpse into his ready-to-launch XMTP, a new communication protocol for Web3, which, if all goes well, will be virtually invisible. (1:44) – Following his curiosity (4:55) – A brother’s impact (6:21) – Baseball (8:09) – Finding music (12:32) – Exploring e-commerce (15:00) – Microblogging (17:25) – Developing Assist (23:33) – Examining company culture (28:03) – Squared Away (35:12) – Escaping San Francisco for Nashville (37:01) – Dealing with anxiety (40:24) – Designing the perfect day (43:50) – Cauliflower gnocchi and Taco Bell (47:05) – XMTP (57:44) – Logos Labs Eric Satz—entrepreneur, serial investor, lover of hot peppers— is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It helps others find the show. Podcast episode production by Dante32.

Moving to the United States from Milan in 2001—mere months before September 11—Lorenzo Thione was quickly forced to reckon with life’s lack of guarantees. The only life worth living was an authentic one. Coming out was a must, and he never looked back. Lorenzo Thione is an entrepreneur, technologist, venture investor, and producer making an impact across several organizations: Gaingels, Sing Out, Louise! Productions, The Social Edge, and StartOut. He is a resolute LGBTQ community advocate and dedicated to amplifying underrepresented voices and stories. In this episode, Lorenzo discusses co-founding StartOut and managing Gaingels, and their respective commitments to LGBTQ entrepreneurs. He reflects on the significance of receiving funding and value from a diverse source and the immense impact of representation. In addition, Lorenzo shares insights into selling a company and assembling a diverse board of directors and leadership team. A true multi-hyphenate, Lorenzo speaks with Eric about his journey developing a Broadway musical alongside George Takei. Weaving his theatrical pursuits alongside his entrepreneurial advice, Lorenzo shares the profound inspiration for Allegiance and an exciting announcement about the future of the musical. (0:39) – Entrepreneur at heart (5:13) – Computer science (7:53) – Feeling different (11:27) – The power of representation (14:59) – LGBTQ advocacy and StartOut (19:18) – Gaingels (26:44) – Going beyond VC (28:46) – Diversifying a board of directors (34:20) – The road to Broadway with Allegiance (47:24) – What’s the hardest thing about being an entrepreneur? (49:54) – Selling a company Eric Satz—entrepreneur, serial investor, lover of hot peppers—is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It helps others find the show. Podcast episode production by Dante32.

When was the last time you read Time cover to cover? This episode’s guest would read and discuss the magazine issues with her father every week as a child. It was an activity she didn’t quite appreciate at the time, but those in-depth discussions provided a foundation for understanding the world beyond Harlem and sparked a lifetime of curiosity and an industry-spanning career. Lorine Pendleton—investor, advisor, and attorney—started her career in the halls of Capitol Records, earned her law degree, and continued her path in startups until discovering an unsettling fact: Less than 1% of venture capital was deployed to Black founders. Today, Lorine is a Lead Investment Partner at Portfolia in the Rising America Funds, which are dedicated to funding historically ignored founders and communities. In this episode, Lorine shares insight into the unique path she has carved through technology, entertainment, and law. Calling upon her investment expertise, she discusses the challenges faced by women, people of color, and LGBTQ individuals in gaining access to and receiving funding. Lorine provides a glimpse into the decision-making process at Portfolia, and she explains the role entrepreneurship can have in shifting wealth, particularly in the next decade. Later in the episode, Lorine shares with Eric several highlights in recent investments, how TIGER 21 is cultivating an empowered network of high-net-worth individuals, and her relationship with angel investing.  (2:22) - “Talent is equally distributed, but opportunity is not.” (7:01) - A father’s influence (9:02) - Harlem in the 70s (10:14) - Moving to the ‘burbs (16:34) - Attending Brown University (20:35) - Capitol Records (25:15) - Exploring the world of startups (27:37) - Pipeline Angels (30:40) - Portfolia (35:58) - The decision-making process (39:11) - Investment highlights (40:30) - TIGER 21 (43:35) - Angel investing Lorine Pendleton is a seasoned investor, business development executive, attorney, and public speaker with extensive experience in the legal, technology, media, and entertainment industries. She is a Lead Investment Partner at Portfolia in the Rising America Funds, the New York Chair at TIGER 21, and a Board Member of the Angel Capital Association. Lorine received a BA from Brown University and a JD from New York Law School. Eric Satz—entrepreneur, serial investor, lover of hot peppers— is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It helps others find the show. Podcast episode production by Dante32.

There's a lot of noise in the investment space—raving pundits, extreme headlines, and financial advertisements—and investors are susceptible. Long-term success requires learning to tune it out. This week’s guest is William Spitz, the highly decorated former Treasurer and Vice Chancellor for Investments at Vanderbilt University and co-founder and principal of Diversified Trust. In this episode, Bill reflects on being immersed in environments of influential and innovative financial thinkers during his MBA at the University of Chicago and in the intercollegiate, collaborative atmosphere of his early years of endowment investing at Vanderbilt. He provides a glimpse of the tremendous ten-fold growth of Vanderbilt’s endowment assets during his 1985–2007 tenure, highlighting the funds that contributed to such staggering growth. Bill and Eric dive into evolving corporate values and the current supply chain crisis. Speaking on personal investing, Bill provides essential advice on harnessing your own knowledge and embracing tinkering while trusting your portfolio. Listen in to learn how Bill manages his own portfolio after his award-winning success in endowment asset management.  (1:21) - A Renaissance man (5:12) - University of Chicago and the early years (9:57) - Return to Vanderbilt (13:14) - The growth of the endowment (16:20) - Sequoia Capital and Kleiner Perkins (18:25) - Longevity (20:38) - ESG investing (23:17) - The share buyback debate (24:28) - Supply chains and inflation (28:04) - Minimizing the damage caused by investment noise (33:41) - Crypto: exchange vs. investment (37:50) - Diversified Trust Company (40:30) - “What do I know vs. the world?” (43:00) - Signs of speculative excess (44:25) - Barbell approach to personal portfolio William Spitz is the co-founder and principal of Diversified Trust Company and serves on the Board of Directors of MassMutual Financial Group. From 1985 to 2007, he was Vanderbilt University’s Treasurer and Vice Chancellor for Investments, increasing the endowment ten-fold. He has subsequently received the Foundation & Endowment Money Management’s Lifetime Achievement Award, NACUBO’s Rodney H. Adams Award, and the Hirtle Callaghan Award of Investment Leadership. William earned a bachelor’s degree from Vanderbilt University and an MBA from the University of Chicago. Eric Satz—entrepreneur, serial investor, lover of hot peppers—is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please follow The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It helps others find the show. Podcast episode production by Dante32.

Promising ideas never really leave you. A visit to a tea auction in India was the missing ingredient Barry Nalebuff needed to create Honest Tea with his former student, Seth Goldman, five years after connecting over disdain for excessively sweet beverages. This week’s guest is renowned Yale School of Management professor, serial entrepreneur, and prolific writer Barry Nalebuff. Following the immense success of Honest Tea, Barry co-founded Kombrewcha and Real Made Foods. His most recent book, Split the Pie: A Radical New Way to Negotiate, was released in March. In this episode, Barry discusses his logical—"Spockian”—approach to negotiation and the key questions to pursuing a win-win result and aligning incentives. He shares insight into the craft of branding and his journey with Honest Tea and subsequent projects.  Later in the episode, Barry and Eric dive into investing with leverage, assessing risk, and maximizing your stock market exposure across time. They consider the nature of dividends on cultural assets and NFTs. Listen in to learn more about Barry’s journey from the classroom to the NBA to his adventures in competitive table tennis.  (2:01) “Cereal” entrepreneur  (6:36) Following logic (7:55) Partnership with Seth Goldman (9:50) Honest Tea (13:00) Teaching game theory and negotiation (16:43) Split the Pie  (21:38) Rule #1 of negotiation (23:27) Creating the pie (27:18) Mission in a Bottle (32:46) Lifecycle investing (39:18) Diversification across asset classes (43:54) NFTs (47:35) Working with the NBA (51:15) Access to alternative assets Barry Nalebuff is the Milton Steinbach Professor at Yale School of Management and co-founder of Honest Tea, Kombrewcha, and Real Made Foods. He has taught negotiation, innovation, strategy, and game theory for 30 years and has co-authored several books—including Thinking Strategically, Co-opetition, and his most recent publication, Split the Pie. Barry is a graduate of MIT and Oxford University, and he serves as director on the board for AGP Group.  Eric Satz—entrepreneur, serial investor, lover of hot peppers— is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It really helps others find the show. Podcast episode production by Dante32.

Imagine navigating the deterioration of the mortgage market in 2007 and facilitating the most high-profile transactions of the financial crisis. Then, imagine that it’s March 2020, and you’re leading the SEC as the COVID-19 pandemic upends the global economy.  This week’s guest has chartered these choppy waters and emerged aiming the lessons of the past at our regulatory future. Jay Clayton served as the 32nd Chairman of the U.S. Securities and Exchange Commission and boasts a decades-long career at Sullivan & Cromwell, where he currently is a Senior Policy Advisor and Of Counsel.  Jay’s career in law stemmed from an interest in business, a route that gave him access to major business decision-making moments. Despite his unexpectedly lengthy tenure at S&C, Jay—whose lineage is dotted with government officials—found himself appointed to lead the SEC by President Trump in 2017.  In this episode, Jay and Eric dive into the architecture of public and private capital markets and the challenging environment for retail investors. Jay speaks on the principles at the core of the Securities and Exchange Commission, particularly the importance of leveling the information playing field and rethinking the definition of an accredited investor. He reflects on the 2017 ICO craze and the precarious economic situation of the pandemic’s early days. Jay shares insights into how to approach emerging financial products from a regulatory standpoint and the crucial question: Bitcoin…commodity or security?  (1:43) – Who is Jay Clayton? (2:29) – The early years (5:09) – Sullivan & Cromwell  (6:35) – Reflections on the financial crisis (9:28) – Arriving in Washington (13:41) – COVID-19’s interruption (15:02) – Rethinking the rules (16:33) – Challenges for public companies (19:41) – The retail investor is missing out (22:45) – How can one qualify as an accredited investor? (24:10) – The architecture of the public markets (26:22) – New requirements (39:11) – What qualifies as a security? (31:57) – Bitcoin = commodity (33:52) – Predicting the crypto regulatory environment Eric Satz—entrepreneur, serial investor, lover of hot peppers— is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It helps others find the show. Podcast episode production by Dante32.

This interview was recorded on February 10, 2022. If you’d asked Mona Sutphen at graduation what her career would look like, she might’ve mentioned a path into the film industry or advertising; somewhere far removed from the public service and community organizing world of her parents. Despite that, at the suggestion of her college advisor, she took the Foreign Service exam upon graduation and then promptly forgot about it, moved to Chicago, and began her career in advertising.  That is until a late-night spreadsheet disaster led to a wake-up call declaration that “there has to be more to life than selling shampoo.” A few weeks later, Mona got the call that she’d passed the Foreign Service exam, sparking a decades-long career in the foreign service and public sector.  This week’s guest is the adventurous, inquisitive Mona Sutphen, former White House Deputy Chief of Staff for Policy under President Obama and current Partner/Head of Investment Strategies at Vistria. Mona grew up in a multiracial, community-oriented family in Milwaukee. In this episode, she shares her insights on working with global decision-makers throughout her distinguished career in public service and her ongoing dedication to problem-solving on the world stage. In the latter half of the episode, Mona discusses the undeniable future of crypto (and its regulation), the evolving ecosystem of decentralized finance (DeFi), and the potential of greater microloan access. Listen in to learn Mona’s essential advice for individuals exploring the crypto world and the necessity of access to investment opportunities. (2:25) Who is Mona Sutphen? (6:24) Leaving Wisconsin for college (9:40) Entering public service (11:42) What is the goal of Foreign Service? (14:38) Competition (and collaboration) on the world stage (19:56) The art of negotiation (24:17) Spotify in the spotlight (25:36) The Clinton and Obama administrations (27:54) A dangerous moment in our country (31:46) Power and investment opportunities (35:43) The crypto landscape (42:31) Microloans and access to capital Eric Satz—entrepreneur, serial investor, lover of hot peppers— is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts, or Spotify. It helps others find the show. Podcast episode production by Dante32.

"I'm in constant search of problems that are big enough and interesting enough that I can dive in and never reach a bottom." – Dror Poleg This week's guest is an economic historian and author, but his multi-hyphenate career includes titles such as real estate private equity exec, startup founder, front-end developer, parliamentary advisor, and soldier. It's a wide-ranging, international career with a resilient, independent, and entrepreneurial thread tying it all together.  In this episode, Dror Poleg talks about the failure of his startup and how he used it as an opportunity to reassess his priorities and values. He went back to the roots of what had brought him success in the past—taking an academic approach, doing the homework, and becoming an expert before trying to build something. What he found was a deep interest in the research itself and a knack for explaining current tech trends and their implications for the business world. This talent for breaking down complex topics, combined with an aversion to the purely opportunistic, or straight fraudulent, actors rampant in the space, led Dror to start Hype-Free Crypto—an online course providing an impartial introduction to the technologies and business models that will define the next decade. Listen to Dror talk about the potential dark side to financial success and the importance of being intentional in investing your time and talent. Be sure to stick around to the end for a crash course in Web3 and NFTs, or check out Hype-Free Crypto for the full curriculum.  (02:04) Who is Dror Poleg? (03:53) My wife has no idea what I do (04:23) You need to have stability in life (08:16) It's not always up and to the right (13:58) Rebuilding a career after failure (17:33) The importance of personal support networks (21:29) A foundation to settle down (23:06) When money leads to a life you don't actually want (26:38) An economic historian and a live events promoter (28:54) The substance under the noise (36:31) What is Web3? (42:13) Conservation of centralization (45:31) Power and radical change (47:38) More than a monkey photo Eric Satz—entrepreneur, serial investor, lover of hot peppers— is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It helps others find the show. Podcast episode production by Dante32.

Lately, each week seems to bring a new headline about yet another hot trend in the alt investment space. It’s easy to get lost in this current wave of alternative investments. In this episode, Michael Sidgmore helps make sense of all these trends by breaking down how they’re playing out within the familiar arena of sports.   Michael has a unique appreciation for the sports world, having grown up playing soccer around the world. It’s an international experience that led to him attending undergrad in London and staying for an accidental gap year with the UK nonprofit Room to Read.  It was a formative time that seeded an appreciation for diverse perspectives and a desire to create an impact that’s threaded throughout his career and evident in how he describes the best parts of being a VC, a job where he’s able to “help build companies everyday that actually impact people’s lives directly.”  Through this lens, it's easy to understand Michael’s earnest enthusiasm for the alt investment space, particularly interest-based investing trends and the ability for individuals to more easily invest directly into the things they’re most passionate about.  Listen in to hear more about the collision of culture and investing across the sports stack, the regulatory changes making it possible, and tips for individual investors ready to jump into alternative investments.  (1:59) Who is Michael Sidgmore? (7:20) Monetizing engagement in sports  (11:33) The power of purpose-driven content  (14:44) A fascinating time for new sports world entrants  (18:50) The fractionalization of assets and the evolution of crowdfunding platforms  (22:55) The upending of fundamental financial models of value (25:45) Moving beyond the 60/40 portfolio  (28:00) Where are we on that adverse selection curve? (33:20) Reg CF: Did we start in the right place with regulatory changes? (41:07) Three important points on diligence  (45:54) When do we stop calling them “alts”? Michael Sidgmore is the co-founder and partner of Broadhaven Ventures, as well as the founder and partner at Sixth Man Capital, the founder of Alt Goes Mainstream, and co-founder of Community x Capital, where he and Alexis Ohanian educate others about the collision of community, culture, and finance. Eric Satz—entrepreneur, serial investor, lover of hot peppers—is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.    If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It really helps others find the show. Podcast episode production by Dante32.

It’s hard to imagine moving on from a self-described $2B mistake, let alone maintaining a positive attitude about it, and yet that’s exactly what this week’s guest did. In this episode, you’ll hear Packy McCormick talk about the winding path that led him to create Not Boring and why over the long run, he believes optimism is the best return strategy. Packy’s resilience and work ethic started early, including with a formative experience bringing home a C+ in French. He grew up in a family that valued hard work and honoring commitments without being too hard-charging; an ethos he carried through studying economics and philosophy at Duke, onto an energy trading desk during the 2008 crash, and then into public finance. Ultimately it was a notable comfort with risk and desire to continue charting his own course that led Packy to leave corporate finance for the NYC startup world in 2013, but not before a brief and ill-fated detour into options trading that would define his venture-focused investing strategy going forward. Listen in to learn more about Packy’s infamous Bitcoin sell-off and how the pandemic timing played into the launch of Not Boring in this week’s episode.  (01:46) Let’s start at the beginning (03:20) How do you run a FinTech in Ghana? (06:15) Clearly a family of ‘underachievers’  (08:53) Relating to your parents once you are one yourself? (13:27) Philly to Durham (16:35) Summer 2008 on the energy trading desk (18:57) The $2 billion dollar mistake (22:59) Just buy and hold (25:49) Startup life in NYC (28:30) Not Boring is born (33:43) Moving Markets (41:18) Will retirement be a thing in 20 years? (44:22) Invest in things you want to learn about (45:37) Optimism as the best long-term return strategy Eric Satz—entrepreneur, serial investor, lover of hot peppers—is the founder and CEO of Alto. The idea behind Alto was born out of a problem. Eric found a clear need to give people more control over their investments (and investment opportunities) in a simple, streamlined way and created Alto to make these opportunities available to all investors, not just the ultra-wealthy or institutional investors.  If you'd like to receive new episodes as they're published, please subscribe to The Altogether Show with Eric Satz in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts or Spotify. It really helps others find the show. Podcast episode production by Dante32.

From lawyer to venture capitalist, this week’s guest is always looking to the future. An optimist with an interest in science fiction, he sees investing as an avenue to create a future in which his daughter will live. This week, you’ll hear Jake Chapman’s journey to co-founding Alpha Bridge Ventures. Despite being pseudo-rejected once for undergrad and another time for law school, Jake persisted and ended up with two degrees from UC Berkeley. His introduction to investing, however, came after law school. At the time, he was working at a firm that represented venture capital companies. It was there that he knew he wanted to “be the principal, not the agent,”and thus he left the firm to start his own business. After several attempts and with growing experience in the industry, Jake decided he wanted to build something big and institutional. Alpha Bridge Ventures was born in 2018 and has been his primary focus ever since. In this episode, Jake provides exclusive advice to founders and shares the stories and passions that made him who he is today. Whether or not you are an entrepreneur, this is a compelling and encouraging listen.

A master negotiator with years of experience in the business world, this week’s guest is as driven as they come. Growing up in a home where autonomy was encouraged and big decisions were made with a consultative approach, he gained his confidence at a young age. This week, you’ll hear how Scott Kitun paved his own way to becoming a media entrepreneur and co-founder of Technori. Scott describes himself as always being “20 years ahead,” which he attributes to sitting in on sales meetings with his father. From the time he was 5 years old, he’s been listening to the nuances of why a person says yes or no to a product or service. His innate ability to see things through the lens of a businessman has helped him value earning relationships and respect. In this episode, Scott walks through his unconventional journey to becoming an entrepreneur－from negotiating his way through college, to realizing commercial real estate wasn’t for him, to building his own curriculum for grad school, and eventually helping make Chicago one of the largest tech ecosystems in the world. His journey to success wasn’t without its setbacks, though, and he’s the first to admit having too many regrets to count. The silver lining to it all? Find out by listening to this week’s episode!

A serial entrepreneur, Matt Mireles is the co-founder and CEO of The Oasis, a synthetic communication company. Hailing from a family steeped in social activism, outdoor adventuring, and professional climbing, Matt’s pursuit of big dreams on an exciting and high-risk path could be expected. Still, you’ll want to buckle in. Get ready for stories of being an EMT in the ghettos of Los Angeles, fighting forest fires while dropping in and out of UC Berkeley, and working as a 911 paramedic in the South Bronx and Harlem to pay for Columbia University and pursue professional journalism. When Matt saw the internet coming to devour traditional media, he left The New York Times and headed to Silicon Valley to launch an internet startup—without any technology or business experience. Not surprisingly, earlier life experiences that required Matt to learn on the fly, wrestle with debt, and stomach success and failure proved valuable. Matt successfully built his first company and sold it in 2012. A second startup failed, followed by several dark years. Finally, the third startup fulfilled the entrepreneurial dream of professional and financial success. In this episode, Matt shares his journey from swashbuckling outsider to Silicon Valley insider teetering on the edge: Jobless, haunted by failure, and drowning in debt. His passion and frank vulnerability make this listen uniquely engaging, and his climb back from the dark days to jubilant success and freedom will have you cheering to hear more.

It takes a lot of courage to leave a secure career to become an entrepreneur, and this week’s guest did just that. His passion for investing changed the trajectory of his dreams, and led him to launch his own company in 2019. In this episode, you’ll hear Steve Walsh talk about being an active angel investor and how he stays motivated in what he calls the entrepreneurial ecosystem. Born into a very traditional blue-collar, middle-class family, Steve was raised on the saying, “You never wanted for anything, but you had to work for everything.” His hard work began in high school when he was doing more than three hours of homework a night on top of an hour-long commute each way. He then went on to graduate from UMass Amherst and complete two educational programs through Harvard. After years of investing, Steve looked at his portfolio and realized something was missing. The only space he wasn’t investing in was alternative assets—early-stage startups to be specific—and thus his love for angel investing was born. As his interest in angel investing grew, so did his vision of becoming an entrepreneur. Now he spends every day in the entrepreneurial ecosystem, and he doesn’t want to spend his life any other way. In fact, his biggest regret is that he didn’t become an angel investor and entrepreneur earlier in life. What’s the number one lesson he’s learned so far? Listen to this week’s episode to find out!

Life is full of difficult moments, but it’s how you choose to approach them that defines you. This week’s guest is known for her optimism and positivity. From struggling with the pressures of adolescence to running a business during the 2008 economic crisis, she has never wavered in her faith that things will get better. In this week’s episode, you’ll hear about Amy Seigenthaler’s perspective on living small, educating big, and traveling often. A Nashville native, Amy found her way to the Northeast, where she majored in English at Boston College before beginning her career as a crime journalist. After 10 years in a career that the normally positive Amy described as "tough on the soul," it was time for a change. So when she received a late-night call from Ambassador Jean Kennedy Smith, asking her to move to Ireland to be her speechwriter, she knew she had to jump at the opportunity. Following the unexpected and tragic death of her father, Amy and her sisters came together to run his PR firm in their hometown. It was here, during the economic crisis, that she realized that if you are driven first by doing the best by your employees and not the bottom line, you will succeed. A working mom of three, Amy discusses what it’s like to be a woman in business and her passion for PR. In this episode, we talk about how Amy not only found her way despite the hardships but also how she never stopped smiling. If you’re in need of a pick-me-up, or just looking for an interesting story (she’s got plenty!), take a listen to this week’s episode.

What does it take to go from small-town kid to successful CEO? To this week’s guest, the answer is simple: never stop learning. A self-proclaimed underdog with a burning desire to make an impact, Ryan Caldbeck describes himself as gritty and a dreamer. In this episode, Ryan discusses growing up in a small town in Vermont, becoming an NCAA basketball champion, finding success in private equity, and eventually co-founding (and stepping down from) CircleUp—and the role each played in his passion for tech entrepreneurship.  Ryan’s small-town upbringing shaped his entrepreneurial spirit. From the time he was young, he would dream about accomplishing something amazing. As his dreams became a reality, though, he found himself struggling both personally and professionally. Reflecting on his journey in admirable detail, Ryan advocates for tapping into your network for support and stresses the importance of mental health. As someone who is extremely curious and loves to learn and grow, Ryan felt stuck in his career in private equity. That all changed in early 2011, while sitting on a panel where no one could answer the question “How do you raise money for a $5MM business?” At that moment, he knew he wanted to start a company that was going to make an impact—and thus, CircleUp was born. Suddenly, he found himself surrounded by people who loved to learn just as much as him, and it was as if his whole life finally made sense. In this episode, we talk about Ryan’s intense passion for human connectivity through learning, his journey to CEO, and his ultimate decision to step down. So, what’s next for this life-long learner? Listen to the full episode to find out.

Investor. Writer. Researcher. Strategist. Family man. This week’s guest wears multiple hats—all at the same time. Known for his blog, podcast, and several books about the craft of investing, Meb Faber’s voice appeals to investors and non-investors alike. Investing is “all about narratives,” Faber says, “Look at historical contexts and global weather, stakeholder interests and your own motivations.” A veteran strategist with a love for reading, Faber is a big proponent of portfolio diversification and learning to be a “value investor.” Born in Colorado, Meb moved around a lot as a boy and landed in North Carolina for his adolescent years. After graduating from the University of Virginia with a double major in Engineering Science and Biology, he changed direction and became an investment strategies expert. Today, he lives in Los Angeles with his wife and three-year-old son. Listening to Meb’s conversation with Eric,  you’ll quickly hear why he is such a natural fit for Alto’s mantra, “you do you.” In this episode, value investor Meb Faber shares market wisdom applicable not only to stocks, bonds, and building your portfolio, but also to life itself, from farming to family and beyond. If you want to know the secret to being ready for the unexpected—take a listen. Anything else you need please let us know! 

Life isn’t always black and white, and sometimes the gray is controversial. This week’s guest firmly believes in staying true to himself,  living by his grandmother’s maxim: “What other people think of you is none of your business.” In this episode, you’ll hear that come to life. When asked to describe himself, he said gratitude, resilience, and enthusiasm. This is a man who now has his own unit of time: Anthony Scaramucci. Anthony was a successful entrepreneur, financier and political player well before stepping up to the podium as White House Director of Communications in 2017—for 11 days. Reflecting on this trajectory with surprising self-awareness, Anthony shares stories of the people and places that gave him the stomach to make mistakes, move past failure and charge forward, living unapologetically big.  For Anthony, choosing risk and testing his resilience are central to being alive, not at all contradictory to being a conservative institutionalist. A blue collar-born elite—educationally, socially and financially—Anthony speaks the vernacular of the person he’s talking to. He knows who he is, but he keeps us guessing. He’s a walking dichotomy, a blend of black and white, and he thrives in the gray.  In this episode, Anthony shares how he loves being an entrepreneur, gains insight from history, loves our country—and firmly believes in the future of digital currency. Listen in to hear his take on the balancing act of life and how people aren’t perfect—so our world won’t be, either. And what would be the fun in that anyway?

Becoming a successful entrepreneur is difficult, but it’s even more difficult if you’re a college dropout. This week’s guest defines “self-made.” From waiting tables to writing (and re-writing) code to becoming an entrepreneur, he’s also self-taught. In this week’s episode, you’ll hear about Marcus Whitney’s personal roller coaster—and how the ride we call life has made him the person he is today.   Marcus faced a low point after (involuntarily) dropping out of college. How was he going to pick up what was left of his confidence and rebuild the future he knew he wanted? Over the course of a few years, he worked to get his life back together—and moved to Nashville. He started waiting tables to pay his bills, and then one day, he heard about “coding.” Fascinated by the idea of a skill that could be learned and didn’t require a college degree to earn a decent income, he moved into the tech world—and that’s where his ride takes off. In this episode, we talk about Marcus’s highest of highs and lowest of lows—and how now, when he looks back, he realizes that immersing himself into technology around the same time as the dotcom boom was the right move for him. If you are in need of a little inspiration, or just a great listen, this interview with Marcus will do the trick.

There are a lot of unique people in this world, but this week’s guest is truly one of a kind. How does someone major in neuroscience at Berkeley, become a lawyer, and then end up as the CEO and co-founder of a wildly-successful investment platform? In this week’s episode, you’ll hear from Kendrick Nguyen on how he made key choices along his insanely untraditional path. Ken was born in Vietnam and moved to the US as a kid — having to learn English as a second language and adjust to new cultural norms. While this isn’t easy for anyone, he had additional challenges when he “skipped a bunch of grades” and attended Berkeley when he was only 12. So in case you couldn’t already tell — he’s pretty fucking smart. In this episode, we talk about how he never wanted to learn about the brain but always wanted to be the brain behind something meaningful. This led him to his role as CEO and co-founder of Republic — an investment platform that connects investors to private deals. Listen in to hear how this incredible human being’s story has unfolded so far — and how there’s still a lot left to tell.