Millennial Masters

📺 Watch now on Substack or YouTube | 🎧 Listen on Spotify or Apple Podcasts This week’s Millennial Master is Joshua Dziabiak, founder and CEO of Perigon. Joshua started building businesses at 14, growing up on a farm in rural Pennsylvania. What began as teaching himself how to design websites turned into a real company, which he sold before most people finish school. He didn’t stop there. He went on to build companies across media, ticketing, insurance, and data, learning firsthand what it takes to start from nothing and what changes once a business is established, scaled, and no longer fragile. One of his businesses passed $100 million in revenue. Another reached unicorn scale, a valuation over a billion dollars. Along the way, Joshua saw how roles shift, and how different the work feels once you move beyond the early building phase. This episode looks at those transitions and what it means to keep building when the stakes, expectations, and tools keep changing. Takeaways from Joshua’s episode 1️⃣ Product does not sell itself Joshua said he still falls into the trap of wanting to perfect the product and the messaging, then assuming people will show up. His point was simple: you can build something great and still lose if you do not have a real plan to tell people about it. If you are early, pick one channel you can repeat weekly, run direct outreach every day, and treat distribution as part of the build. 2️⃣ Distribution is your defence Spend more time on distribution than on “latest and greatest” features because the noise can distract you and mess with your confidence. You win by getting embedded where people already work, so they set it up once and do not need to live in your dashboard. If you are building a tool, make the setup sticky, make it easy to plug into what they already use, and aim for usage that keeps running without you asking for attention. 3️⃣ Build so one AI update can’t wipe you There are two risks in this space: a big player ships your feature, or the market solves the same problem in a new way you did not see coming. The move is to lean into distribution, so you are not relying on a single shiny feature to protect the business. For founders, that means getting your product wired into how customers already work, owning the relationship with the customer, and charging for outcomes people keep needing even when the tools change. 4️⃣ Choose investors like you choose a spouse Joshua learned the hard way that investors do not all want the same outcome, even when they say they do. Some want a smaller win on a shorter timeline. If you do not ask, you end up confused when they push you in a direction that does not match your own plan. His fix was to align early on the size of outcome, timeline, and how much capital the journey really needs, then only take money from people who can back that path. 5️⃣ Slow down on co-founders and early hires Your first hires and co-founders can make or break the business and your own motivation, so you cannot rush it. They should complement you, not mirror you. If you are picking a co-founder or first key hire, test working together under pressure, agree on how decisions get made, agree on what “good” looks like, and look for someone strong where you are weak. In this episode we cover: 00:00 Introduction to Joshua Dziabiak 02:09 Starting a business at 14 on a Pennsylvania farm 06:25 How early success reshaped risk and money 08:48 The failed record label that led to a $100m company 11:23 Building ShowClix before platforms made it easy 13:58 The moment building stopped being the job 16:39 What scaling past $100m actually feels like 19:14 Picking investors without breaking the business 21:30 Walking away when everything looks fine 23:56 Why he chose insurance to build a consumer brand 31:38 How marketing incentives broke trust online 33:43 Building Gawk to fight misinformation 38:37 Why Perigon moved from consumer to enterprise 43:12 Building products while AI keeps changing the rules 50:56 Where founders quietly slow their own companies 55:40 The hiring decision founders regret most Get full access to Millennial Masters at millennialmasters.net/subscribe