Podcast Summary: How to Money – Episode #1000: Ask HTM Anything!

Introduction

In the milestone 1000th episode of How to Money, hosts Joel and Matt pivot from their usual financial discussions to a special "Ask Me Anything" (AMA) format. This celebratory episode delves into a variety of personal topics, offering listeners an intimate glimpse into the hosts' lives beyond personal finance. Released on June 23, 2025, the episode marks a significant achievement for the podcast, underscoring its commitment to providing relatable and unbiased financial guidance.

Celebrating 1000 Episodes

From the outset, Joel and Matt express their excitement and gratitude for reaching this monumental milestone. Joel muses on their journey, saying, "Who else would you celebrate it with? There's no one else" ([03:04]). Matt echoes this sentiment, highlighting the unpredictability of hitting 1,000 episodes and emphasizing the role of their loyal listeners: "For some reason they love us or like us enough" ([03:27]).

Listener Questions and Hosts' Answers

The heart of this episode revolves around listener-submitted questions, which range from light-hearted inquiries to deeper, more personal topics. Joel and Matt aim to address as many questions as possible, fostering a sense of community and transparency with their audience.

Life and Career Questions

One listener, Allison, proposed a creative idea: "Why don't you and Matt go on a nationwide tour and hang, party, barbecue, drink, craft beer all around the country" ([07:12]). Joel responds positively but notes the logistical challenges, especially with family responsibilities: "The tough thing, it's gonna be hard to, like, leave the fam for that long" ([07:26]).

Travis asked about the best half marathons in Georgia suitable for runners accustomed to New York weather. Joel recommended the Helen Trail Half Marathon, praising its scenic mountainous trails and favorable April conditions: "It's beautiful... a great time of year where it's kind of cool, but it's not cold and it's not hot" ([16:11]).

Personal Interests and Hobbies

Rebecca inquired about the hosts' favorite board games. Matt proudly declares his love for "Settlers of Catan" ([12:20]), while Joel shares his preference for "King Domino" and "Acquire," highlighting the strategic and unpredictable elements that make these games engaging ([13:10]).

Jenny's question about opening a brewery reveals Joel and Matt's appreciation for craft beer and community-focused spaces. Joel envisions a brewery known for its friendliness and hazy IPAs, aiming to create a welcoming environment: "Just being super friendly with everybody who walks in and having a community, like a cheers-like joint" ([10:07]). Matt adds his dream of incorporating local farm ingredients and natural scenery, inspired by breweries like Hill Farmstead and Jester King ([11:28]).

Friendship Dynamics

Jeffrey posed a question about whether Joel and Matt ever get on each other's nerves and how they navigate such moments. Matt emphasizes the importance of prioritizing their friendship over business: "Working with your best friend can work as long as you prioritize the friendship above the business" ([32:16]). They discuss the depth of their bond, likening it to a familial relationship and stressing the significance of mutual respect and space: "Neither you nor I have brothers... it helps to, you know, you kind of overlook the different flaws that maybe the other guy has" ([38:28]).

Family and Parenting

Leslie's question about predictions for their children's futures leads to heartfelt reflections. Joel hopes for his children's enduring bonds and observes, "I think our oldest girls will retain it more than any of the rest of them" ([52:21]). Matt shares his aspirations for a large, joyful family, expressing a desire to become a grandparent and to see his children flourish: "I think that our boys are three days apart... I wish I would have been more thoughtful about that" ([52:27]).

Bucket Lists and Regrets

Jenny asked about creating a bucket list, prompting Joel to share his aspirations, such as a hot air balloon ride and hiking the Camino de Santiago with his father: "Hot air balloon ride... I want to hike the Camino. Santiago, preferably with my dad" ([19:26]). Matt expressed his reluctance towards bucket lists, preferring organic experiences over structured goals: "I hate the bucket list methodology" ([19:35]).

In response to the question about regrets, Joel reflects on the importance of taking responsibility and approaching loved ones with humility: "The biggest thing I've learned... to take more responsibility for my actions and to approach the people I love with more humility" ([66:23]). Matt emphasizes personal growth through past mistakes: "You can't you take, like, the judo move and, like, use the momentum of that bad decision to make" ([66:22]).

Miscellaneous Questions

Katie's query about collecting local folk art leads Joel to offer practical tips: "Try to find a festival in your area... you'll find it. You'll be exposed to a bunch of new folks" ([47:50]). Matt contributes by suggesting local galleries as a venue to discover and support artists.

Megan's question about becoming an expert in something obscure had Matt contemplating woodworking and the blend of form and function, while Joel expressed interest in gardening despite not having a green thumb: "I would love woodworking, but highly... What better way to enjoy something than using it" ([50:23]) and "If I was instantly an expert at gardening and I could like do it flawlessly, that'd be kind of cool" ([51:42]).

Discussion on Sabbatical Plans

Towards the episode's conclusion, Joel and Matt discuss their upcoming sabbatical plans. Joel expresses excitement about slowing down and enjoying the mundane joys of life: "Just some time alone and... experiencing the joy in the mundane" ([73:02]). Matt looks forward to embarking on an East Coast road trip with his family, appreciating the opportunity to explore and create lasting memories: "We've never taken a longer road trip... we've been getting more and more into the planning aspect of it" ([71:29]).

Conclusion

As they wrap up this extensive AMA episode, Joel and Matt reiterate their gratitude towards their listeners and share their excitement for the break ahead. They encourage listeners to continue engaging with the podcast and hint at returning with fresh content in early August. Concluding with heartfelt messages and a touch of humor, the hosts reflect on their enduring friendship and the journey that brought them to this significant 1000-episode milestone.

Notable Quotes

• "Who else would you celebrate it with? There's no one else." — Joel ([03:04])
• "If you really want to see joy, then I think it is going to involve a certain amount of letting down, putting aside what you care about the most in favor of watching other people and helping other people in your life succeed." — Joel ([68:35])
• "Working with your best friend can work as long as you prioritize the friendship above the business." — Matt ([38:28])
• "The toughest thing, it's gonna be hard to, like, leave the fam for that long." — Matt ([07:26])
• "I hate the bucket list methodology." — Matt ([19:35])

Timestamp Highlights

• [07:12]: Listener Allison suggests a nationwide tour combining fun and fundraising.
• [12:20]: Rebecca asks about favorite board games; Matt favors "Settlers of Catan."
• [10:07]: Discussion on opening a community-focused brewery.
• [38:28]: Matt on maintaining friendship dynamics while working together.
• [52:21]: Predictions for their children's future relationships and careers.
• [66:23]: Joel reflects on personal growth and regrets.

This comprehensive episode not only celebrates a significant milestone for How to Money but also deepens the connection between the hosts and their audience by sharing personal stories, aspirations, and reflections. Whether you're a long-time listener or new to the podcast, episode #1000 offers valuable insights into the lives of Joel and Matt, enriching the overall How to Money experience.