One Bad Deal Changed My Whole Path – Connor Paddon
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03/03/2025
Show Notes:
INTRODUCTION
What if dropping out of high school could lead you to entrepreneurial success? Meet Connor Paddon, who did just that—transforming from a poker-playing dropout to a thriving business owner and investor. In this episode, Connor shares his journey of starting and selling multiple businesses, including an SEO agency and a scheduling software company. But here’s the kicker—his current passion lies in acquiring “boring businesses” that are anything but dull. If you run a home service business, this is the same ground fractional CFO services for home service businesses covers for the trades.
Connor dives into the art of finding and evaluating these hidden gems, offering golden advice for aspiring entrepreneurs. From leveraging relationships over brokers to navigating the roller coaster of business ownership, his insights are invaluable. So, if you’re ready to learn how to turn conventional wisdom on its head and discover the potential in the mundane, tune in now.
ABOUT CONNOR PADDON
Connor Paddon is a resilient entrepreneur with a diverse background in business. He dropped out of high school to pursue professional poker, which led him to create a website teaching others how to play. This experience sparked his interest in search engine optimization, culminating in his first successful venture – an SEO agency that he later sold. Connor then co-founded a scheduling software company called OnSched, which faced numerous challenges but ultimately succeeded, especially during the COVID-19 pandemic. Despite personal setbacks, including the loss of his father and business partner, Connor managed to stabilize and sell the company.
Currently, Connor is focused on acquiring “boring businesses” through his company, New Age Ventures. He looks for established companies with $1-5 million in EBITDA, 10+ years of operation, and healthy profit margins. Connor’s approach emphasizes building relationships with potential sellers, often through unconventional means such as chance encounters at airports. He values businesses with strong asset bases and seeks opportunities where he can add value through strategic management and talent acquisition. Connor’s entrepreneurial journey showcases his ability to adapt, persevere through challenges, and identify unique opportunities in various industries.
LESSONS LEARNED
1. Resilience in entrepreneurship
Connor’s journey demonstrates the importance of perseverance in business. Despite facing numerous setbacks, including a struggling startup and the loss of his father/business partner, he continued to push forward. This resilience allowed him to overcome challenges and ultimately find success in his ventures.
2. Pivoting business strategies
Connor’s ability to adapt and change directions was crucial to his success. He pivoted multiple times with his scheduling software company before finding a profitable niche. This flexibility allowed him to navigate market changes and find opportunities where others might have given up.
3. Asset-based business acquisitions
Connor emphasizes the value of acquiring businesses with strong asset bases. He looks for companies where the sum of the parts (assets) is close to or exceeds the purchase price, providing a safety net and financing advantages. This strategy offers protection against potential business downturns and easier access to asset-based loans.
4. Building relationships for deals
Connor’s approach to finding business acquisition opportunities through personal connections stands out. By engaging in conversations with business owners he meets through his aviation hobby or other circumstances, he’s able to uncover off-market deals and build trust with potential sellers, often leading to more favorable terms.
5. Delegating and scaling
Connor’s strategy for scaling involves learning the business thoroughly, then delegating to capable leaders. He plans to run acquired businesses for 6-12 months before handing over operations to skilled managers, allowing him to focus on further acquisitions and growth. This approach enables him to expand his portfolio while ensuring each business has dedicated leadership.
QUOTES
“I think starting at such a young age was a huge advantage for me because there was almost not even a concept of failure. It was like, oh, this is just. This didn’t work or this loss, and I got to figure out something else.”
Connor’s early start in entrepreneurship fostered resilience and a problem-solving mindset, viewing setbacks as learning opportunities rather than failures.
“To me a boring business is, you know, things that have been around a long time, things that you know, have a ton of competition out there, but it doesn’t really matter. It’s an essential service maybe.”
Connor defines “boring businesses” as established, competitive industries providing essential services, highlighting the potential in traditional business models.
“I love those off market deals too. I don’t know if any of your audience is interested in that world of buying the small business, which I personally think is great, better than starting.”
Connor emphasizes the value of acquiring existing small businesses over starting from scratch, particularly through off-market deals built on relationships.
“Just don’t leverage up too much. We made that mistake and, and it wound up really hurting us. So be careful. Leveraging businesses and adding a bunch of debt, it can hurt you down the line.”
Connor cautions against excessive leveraging, drawing from his own experience to highlight the potential long-term risks of taking on too much debt in business.
FUN FACTS
• Connor Paddon dropped out of high school to become a professional poker player, which led him to build a website teaching others how to play online poker and eventually start an SEO agency.
• Connor owns a Cirrus SR22 airplane and has been flying for about 10 years, using his pilot’s license to travel around the United States.
• In one of Connor’s current business acquisition deals, he’s working on a $40 million transaction where the seller is willing to finance over 80% of the purchase price due to their established relationship and trust.
TAKE ACTION
1. Build relationships with business owners. Connor found acquisition opportunities by chatting with people at airports and job sites. Start conversations with business owners you encounter – you never know where they might lead.
2. Look for businesses with asset protection. Connor seeks companies where the assets are worth close to the purchase price. This provides a safety net if things go wrong. When evaluating businesses, consider the value of their physical assets.
3. Develop resilience as an entrepreneur. Connor faced many setbacks but kept pushing forward. Adopt the mindset that obstacles are learning opportunities, not reasons to give up. Stay committed to your goals even when facing challenges.
MAXIMS TO LIVE BY
1. Embrace Resilience: Don’t give up when faced with challenges; keep pushing forward to reach your goals.
2. Build Relationships: Networking and forming connections can lead to unexpected business opportunities.
3. Learn from Failures: View setbacks as learning experiences and opportunities for growth.
4. Stay Adaptable: Be willing to pivot your business model when necessary to meet changing market demands.
5. Trust Your Instincts: Sometimes gut feelings can guide you towards the right business decisions.
6. Protect Your Downside: Always have a backup plan or exit strategy in case things don’t go as expected.
7. Value Legacy Over Money: Consider the long-term impact of your business decisions, not just immediate financial gains.
8. Seek Off-Market Deals: Building relationships can lead to unique business acquisition opportunities outside of traditional channels.
9. Understand Asset Value: Look for businesses where the sum of the parts is worth as much or more than the whole.
10. Delegate Effectively: Learn to hand over control to capable team members to scale your business.
11. Invest in Relationships: Take time to build trust with potential sellers; it can lead to better deal terms.
12. Be Patient: Good deals often take time to materialize; don’t rush into decisions.
13. Look Beyond Financials: Consider factors like employee retention and business legacy when evaluating acquisitions.
14. Stay Curious: Always be open to learning new skills and exploring different business models.
15. Leverage Seller Financing: Use creative financing options to reduce your upfront capital requirements.
16. Focus on Profitability: Prioritize businesses with healthy profit margins to provide a buffer against market fluctuations.
17. Seek Stability: Look for businesses with a proven track record of longevity and consistent performance.
18. Be Transparent: Open communication builds trust with both sellers and employees.
19. Understand Your Limits: Know when to bring in outside expertise to complement your skills.
20. Find Your Niche: Identify specific industries or business types that align with your interests and expertise.
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