1619: The Art of the Approach: How to Talk to Anyone About Your Business w/ Kyle Simonett
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RSS Feed Ever felt a personal frustration so deeply you just had to build a solution for it? That’s exactly what Kyle Simonett did. In this episode, Kyle shares his incredible journey from being a ski instructor and Naval helicopter rescue swimmer to a tech entrepreneur solving a major headache for golfers everywhere. He breaks down how he and his co-founders identified the universal problem of booking tee times and built Putting It Close, a platform that automates the entire process.
This episode is a masterclass in turning a passion into a scalable business. For wantrepreneurs and entrepreneurs, Kyle’s story is packed with lessons on the power of a non-linear career path, the critical importance of obsessing over your target customer, and the mindset required to take the leap from idea to execution. You’ll learn why focusing on the end-user is more valuable than chasing big corporate partnerships and how to build a business by solving a problem you genuinely care about.
💡 What You'll Take Away For YOUR Business
- How Your "Unrelated" Past Experience Is Your Secret Weapon: Learn how Kyle’s skills as a rescue swimmer and ski instructor—like problem-solving under pressure and talking to anyone—directly translated into his success as an entrepreneur.
- The Power of Solving Your Own Problem: Discover the process of identifying a personal pain point and scaling the solution to serve a massive audience, moving from a "me" problem to a "we" business.
- Customer Obsession Over Corporate Partnerships: Understand why Kyle and his team chose to champion the individual golfer instead of chasing partnerships with large golf course management companies, and how that focus drives every business decision.
- A Smart Freemium Model to Build Trust & Scale: Learn how Putting It Close strategically uses a free tier to prove its value, attract a user base, and create a natural funnel for its premium subscription.
- How to Network Without Being "Salesy": Get Kyle’s simple but effective technique for starting conversations with potential customers in a genuine way that leads to real relationships (hint: it involves free golf tees).
- Why You Need to "Cannonball" Into Your Idea: Unpack the mindset of taking calculated risks and diving headfirst into your venture, rather than endlessly "testing the waters."
📝 About Kyle Simonett
Kyle Simonett is the co-founder of Putting It Close, a tech platform designed to help golfers find and book hard-to-get tee times effortlessly. His career path has been anything but linear, with experiences as a ski instructor, a Naval helicopter rescue swimmer, and a corporate IT professional for Lockheed Martin. This diverse background equipped him with a unique blend of communication, problem-solving, and technical skills. While earning his MBA, Kyle combined his passion for golf with his knack for solving complex problems to create a solution that serves thousands of golfers across the country.
🎯 Kyle’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
“You need to cannonball into the waters and give it a go. If you don't, you're always gonna sit there and regret not taking that chance.”
📢 Memorable Quotes
- “Our clientele is the golfer... Our primary purpose is to help the golfers get out and get on the course and spend less time searching.” – Kyle Simonett
- “One of the things that I learned with entrepreneurship is you have to try and find a problem and then use your knowledge of the issue… and figure out a way to solve it.” – Kyle Simonett
- "People get hung up on the fact that rejection is awkward... If they say no, that's great. You move on, you go to the next, and you chalk it up as what it is." – Kyle Simonett
💡 Actionable Takeaways
- Solve a Problem You Know: Identify a recurring frustration or inefficiency in your own hobby or daily life. This is often the most authentic and powerful source for a business idea.
- Define Your #1 Customer: Clearly identify who you serve. Write it down and make every decision—from product features to marketing—with that single person in mind.
- Create a Low-Stakes Conversation Starter: Develop a simple, non-pushy way to talk about your business, like Kyle’s branded golf tees. Offer value first before you ask for anything.
- Implement a Free Tier: If your business model allows, consider offering a free version of your product or service to lower the barrier to entry, prove your value, and build a loyal user base.
- Take One "Cannonball" Action This Week: Instead of just thinking about your next step, commit to one bold action that moves your business forward, even if it feels scary.
🔗 Links & Resources
