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Matt Dodge | CEO & Founder of Sigars.com

Damn Good Day 

Matt Dodge is the CEO and founder of Sigars.com. Sigars.com is a B2B Tobacco marketplace specializing in exclusive labels and customization. Ian Lenhart is the Co-founder of Sigars.com and together they discuss the key learnings from their journey of building a cigar business with Sigars.com.

Part I

The podcast episode begins with the hosts expressing excitement about their new studio and how much it has transformed over the past six months. They discuss the changes they’ve made, such as adding a pool table and mentioning the pleasant greenery in the studio.

The hosts reminisce about their history, mentioning that one of them initially lived with a friend named Chris in Miami before moving to their current place. They credit their friend Haley with helping them find a property, which marked their entry into real estate. They highlight the advantages of investing in real estate, particularly in the Miami area, if the right location is chosen.

They talk about a previous apartment, describing it as stylish and suited for artistic endeavors. However, they emphasize that the current house is even more versatile and serves as a tool for various activities such as podcasting, ice baths, and enjoying cigars.

The hosts emphasize the importance of having a space for creative endeavors and mention the benefits of the current house, including ample natural light and a convenient location close to restaurants and other amenities.

Introductions are made, with one host being the CEO and founder of cigars.com, the other being the co-founder of the same venture, and another individual being introduced as “Mr. Does It Everything.” They refer to themselves as “The Gang” or “The Boys.”

Overall, the podcast script covers the hosts’ excitement about their new studio, the transformation of their living space, their journey into real estate, the value of a creative space, and introductions of the individuals present in the episode.

Part II

In the second part of the podcast, the hosts discuss their journey with their company B2B Cigars, and reflect on how quickly time has passed since its inception in late 2021. They emphasize the success the company has achieved in its short existence and express their excitement about the direction it’s heading.

The hosts talk about their unique partnership and mention that they’ve known each other for over two decades, creating a solid foundation for their business collaboration. They acknowledge the common advice against doing business with friends but argue that their long-standing relationship sets them apart.

They recall their early experiences working together, including a job selling soda and water at a baseball stadium. They share the lesson they learned about not letting self-consciousness hinder their sales efforts and how this experience has influenced their entrepreneurial mindset.

The hosts elaborate on their love for cigars and the industry, emphasizing its distinct nature compared to addictive substances like vaping or cigarettes. They discuss how cigars offer a way to invest time in relaxation, connection, and self-care. They clarify that while cigars may not be considered healthy, they view them as occasional indulgences that offer unique benefits.

They discuss the concept of vices and moderation, highlighting the idea that occasional enjoyment of certain activities can be balanced with a healthy lifestyle. They use the analogy of enjoying healthy eating most of the time but indulging in comfort foods occasionally.

The podcast touches on the nature of vices like coffee and unhealthy food, where overconsumption can lead to desensitization to their effects. They argue in favor of occasional indulgence as a way to maintain sensitivity to these experiences.

The hosts briefly mention an Italian restaurant called Borty, describing their occasional splurges on delicious but less healthy foods and desserts.

Overall, this part of the podcast focuses on their business journey, their friendship, their early experiences in the workforce, the appeal of cigars as an occasional pleasure, and the balance between moderation and indulgence in various aspects of life.

Part III

In this segment of the podcast, the hosts shift the conversation to a discussion about eating habits and their own experiences. They talk about overindulgence in rich or unhealthy foods, sharing stories about eating large portions of food and the struggle of resisting the urge to finish it all. One host mentions that they’ve never intentionally eaten bad food and then spit it out as a way to avoid the consequences.

They discuss the idea of self-control when it comes to food and how small actions like stopping halfway through indulgent meals can make a difference. They emphasize the importance of maintaining a positive mentality and not being too hard on oneself. They mention that even if they make a mistake in their eating choices, they can always make up for it with exercise or healthier decisions.

One host shares that they occasionally experience periods of low energy and how these moments can affect their mindset. They highlight the need to be kind to oneself and find ways to break out of such negative phases.

The conversation shifts towards the concept of working smarter rather than harder. They give an example of a recent experience where one host realized they were spending a lot of time on a certain task without making progress. They explain the importance of recognizing when a different approach might yield better results and how this mindset can be applied to various aspects of life.

Overall, this part of the podcast delves into discussions about eating habits, self-control, maintaining a positive mindset, and the importance of working smartly to achieve desired outcomes.

Part III

In this part of the podcast, the hosts discuss the concept of working smarter instead of harder. They talk about how successful business owners and entrepreneurs focus on efficiency rather than just putting in long hours. They mention the rise of AI and automation in the business world and how it can streamline processes but also emphasize that the value of personal relationships can’t be automated.

The conversation then shifts to one host’s ability to communicate effectively and clearly through emails and responses. They attribute this skill to their early experiences as a sports agent, where they had to navigate challenges due to their age. They explain that being younger than the athletes they represented required them to communicate precisely and concisely to earn respect and attention.

The host discusses their approach to communication, which involves getting their point across and making requests in the shortest amount of time possible. They view this approach as a way to achieve their goals effectively and efficiently.

Overall, this part of the podcast focuses on the importance of working smart, adapting to challenges, and effectively communicating to achieve goals, especially when faced with obstacles like age-related biases.

Part IV

In this segment, the hosts delve into the challenges of being a sports agent and highlight the necessity of integrity and standing out in a field that can sometimes be seen negatively. They discuss the misconception that sports agent work is glamorous, influenced by portrayals in media like movies and television shows, but emphasize that the reality is much different.

The conversation shifts to the host’s early days as a sports agent and how they managed to get their foot in the door despite the industry’s skepticism about their age and experience. They share their strategic approach of contacting an agent’s office, initially pretending to be an athlete interested in representation, and then being transparent about their intentions. This unconventional approach earned them an opportunity for an internship in New York City.

The host recalls working as an intern in New York City for two and a half years, which marked the beginning of their journey in the sports agency field. They talk about managing their first athlete during that time, highlighting the significance of that experience in shaping their career trajectory.

Overall, this segment of the podcast discusses the challenges and misconceptions of the sports agent industry, the host’s creative approach to gaining opportunities, and their early experiences working as an intern in New York City, which laid the foundation for their career in sports agency.

Part V

In this portion of the podcast, the hosts discuss the strategy of getting their foot in the door by offering to work for free in order to gain valuable experience and education. One host shares their personal experience of reaching out to a successful individual and expressing their willingness to work for free in exchange for learning opportunities. This led to a task that they successfully completed, opening the door for more opportunities.

They emphasize the importance of this strategy, especially for young people or college students who want to learn about a specific industry or field. They suggest that this approach can lead to invaluable education and skill-building that formal education might not necessarily provide.

The hosts also touch on the concept of generational wealth and how education plays a crucial role in passing down knowledge and skills to the next generation. They discuss the idea that on-the-job education and real-world experience can be more valuable than traditional formal education. One host mentions their perspective on formal education, stating that they are not a strong believer in it and that they’re considering alternative options for their own child’s education in the future.

The discussion concludes with them pondering the decision to invest in formal education versus providing opportunities for practical learning experiences, such as starting a business or investing in real estate.

Overall, this part of the podcast delves into the value of practical education, the benefits of on-the-job learning, and the considerations around investing in formal education versus other forms of skill-building.

Part VI

In this segment of the podcast, the hosts discuss the challenges and societal pressures associated with pursuing higher education, particularly the issues related to student debt. They express their concerns about the broken system of student loans, the high-interest rates, and the long-term consequences of debt. They emphasize that the pressure to attend college and the financial burden it can create are issues that need more attention.

The hosts reflect on the societal pressure placed on high school students to attend prestigious colleges and how that pressure can lead to making potentially expensive decisions without fully considering the consequences. They mention that while formal education can provide certain experiences and social interactions, the practical skills and knowledge gained from on-the-job learning can be equally valuable, if not more so.

The conversation then transitions to the host’s experiences in their own entrepreneurial endeavors, particularly in the cigar business. They discuss the origin story of their venture, how they were inspired by watching UFC fights while smoking cigars, and how they saw an opportunity to turn their passion into a business. The hosts talk about the growth of their business and the importance of building genuine relationships in the process.

Overall, this portion of the podcast explores the issues surrounding higher education, student debt, and societal pressures, as well as the hosts’ personal experiences in entrepreneurship and building meaningful relationships through their cigar business.

Part VII

In this segment, the hosts continue their discussion about their entrepreneurial journey, specifically focusing on how they decided to start a cigar business that involved their dads, who were nearing retirement. They reflect on the idea of flipping the script by introducing their dads to a new venture that goes beyond their traditional careers.

The hosts recount the origin of their cigar business and how they came up with the concept while watching UFC fights and smoking cigars. They emphasize the authenticity and organic nature of the idea, stemming from their personal experiences of enjoying cigars with their dads. They share that they initially invested $5,000 to start the business and highlight the importance of building relationships and offering a quality product.

The conversation touches on their pivot from athlete-branded cigars to custom cigars for various brands, along with their engagement in charitable initiatives like Folds of Honor. The hosts talk about the importance of being open to change, embracing pivots, and not being afraid to try new things. They mention that adaptability is crucial for a lean startup and that they have revamped their website multiple times to ensure a strong online presence.

The discussion showcases their entrepreneurial mindset, willingness to evolve, and their ability to turn their passion into a successful business venture while involving their families in the process.


In this segment, the hosts delve into various topics related to entrepreneurship, language learning, and their perspectives on life and business.

They discuss the nature of startups and how many people tend to give up on their entrepreneurial ventures before they even have a chance to gain traction. They mention examples like Dave Portnoy from Barstool Sports, who persevered for 12 years before achieving significant success. They emphasize that persistence is crucial in the world of startups and that being in the game for the long haul significantly increases the chances of success.

The hosts then transition to a personal anecdote about learning Spanish. One of the hosts talks about taking Spanish lessons and building a strong relationship with their Spanish teacher, who genuinely cares about their progress. They highlight the importance of language skills, particularly in their industry where relationships with Spanish-speaking countries are essential for their business.

The conversation also touches on the privilege of living in a country like the United States and the opportunities it affords. They discuss the freedom and advantages of living in America and encourage people to appreciate and utilize these benefits, while also acknowledging the issues that exist within the country.

Overall, this part of the discussion showcases their perspectives on persistence, language learning, cultural experiences, and the opportunities available to them as entrepreneurs in the United States.

Part IX

In this part of the conversation, the hosts continue to discuss various aspects of their lives and experiences. They touch upon the value of learning different languages, especially when it comes to building relationships and conducting business with people from other cultures. They emphasize the benefits of being open to new experiences and expanding one’s horizons by traveling and learning languages.

They talk about the process of starting a business and how important it is to be persistent and resilient, even when facing challenges and setbacks. They also mention the significance of timing and luck in the entrepreneurial journey, and how sometimes things fall into place when the right opportunities arise.

The conversation takes a light-hearted turn as they discuss personal choices, like owning jewelry and chains. They share anecdotes about their experiences and how certain items like chains passed down through generations, hold sentimental value.

The hosts reflect on the different places they’ve lived and the diverse experiences they’ve had, highlighting the importance of intentionally seeking knowledge and learning from every interaction.

Throughout this segment, they explore various themes including language learning, the entrepreneurial journey, personal experiences, and the importance of embracing the journey rather than just focusing on the destination.

Part X

In this final part of the conversation, the hosts reflect on the importance of appreciating the journey rather than just focusing on the destination. They discuss the idea that life goes by quickly, and it’s essential to enjoy the present moment and celebrate the wins along the way.

They talk about the upcoming milestone and success they are close to achieving and express their excitement for the journey they’ve been on together. They emphasize the value of strong friendships and connections with people who have been with them since the beginning.

The hosts touch on the new initiative they are working on involving lasers for their business and how it will contribute to their offerings and growth.

The conversation concludes with a hypothetical question: If Matt Dodge could go back in time and advise his younger self when he was working at the ValleyCats Stadium, what advice would he give? He shares that he would advise himself to trust his gut instincts, both in pursuing positive opportunities and in recognizing when something isn’t the right fit. He emphasizes the importance of doubling down on what feels right and moving on from what doesn’t.

Overall, this segment encapsulates themes of personal growth, trusting intuition, celebrating successes, and cherishing the journey of life.

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