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Millennial Masters

Millennial Masters

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Real talk, real tips. Tune in for insights from millennial entrepreneurs and leaders on business, productivity, and personal growth you can use today.

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Episodios
  • The true cost of scaling 🧱 | Joshua Dziabiak (Perigon)

    The true cost of scaling 🧱 | Joshua Dziabiak (Perigon)
    Jan 13 2026
    📺 Watch now on Substack or YouTube | 🎧 Listen on Spotify or Apple PodcastsThis 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 episode1️⃣ Product does not sell itselfJoshua 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 defenceSpend 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 youThere 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 spouseJoshua 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 hiresYour 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 Dziabiak02:09 Starting a business at 14 on a Pennsylvania farm06:25 How early success reshaped risk and money08:48 The failed record label that led to a $100m company11:23 Building ShowClix before platforms made it easy13:58 The moment building stopped being the job16:39 What scaling past $100m actually feels like19:14 Picking investors without breaking the business21:30 Walking away when everything looks fine23:56 Why he chose insurance to build a consumer brand31:38 How marketing incentives broke trust online33:43 Building Gawk to fight misinformation38:37 Why Perigon moved from consumer to enterprise43:12 Building products while AI keeps changing the rules50:56 Where founders quietly slow their own companies55:40 The hiring decision founders regret most Get full access to Millennial Masters at millennialmasters.net/subscribe
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    58 m
  • I replaced my team with AI to survive 🛠️ | Anjeanette Carter (Stratis)

    I replaced my team with AI to survive 🛠️ | Anjeanette Carter (Stratis)
    Jan 5 2026
    📺 Watch now on Substack or YouTube | 🎧 Listen on Spotify or Apple PodcastsThis week’s Millennial Master is Anjeanette Carter, who has built and lost more than one career.She began as an actor, moved into YouTube, then into writing. At one point, she was earning serious money online, before that income disappeared and forced her to rethink everything she was doing.Today, she runs Stratis Media, a copywriting and LinkedIn personal branding business for founders and CEOs. From the outside, it looks like a straightforward pivot. In reality, it came from a period of pressure, uncertainty, and a market that shifted faster than her business model could keep up with.What makes Anjeanette’s story worth paying attention to is how she responds when a model stops working. When AI began reshaping her industry, she did not wait for reassurance or permission. She restructured the business around herself and AI, letting go of her team in order to keep the company viable.That decision reshaped how she works and how she thinks about leverage, visibility, and resilience. It also changed where she puts her time, her energy, and her attention.This episode looks at what actually keeps a business alive when tools change, platforms shift, and familiar paths disappear. It is about adapting and the skills that continue to matter even as everything around them moves.🔗 Find Anjeanette on LinkedIn, Instagram & SubstackTakeaways from Anjeanette’s episode1️⃣ Sales is what keeps the lights onWhen work dries up, the ability to sell is what buys you time. Founders who can find clients, have conversations, and close deals stay in control when everything else shifts. Relying on platforms, referrals, or luck leaves you exposed the moment demand slows.2️⃣ Personal branding gives you optionsPeople trust people, not companies. When your name carries weight, it becomes easier to attract clients, test new offers, and move direction without starting from zero. This matters most when your business model needs to change.3️⃣ AI only helps if you know what good looks likeFaster tools don’t fix weak thinking. Results improve when you already understand quality, structure, and outcomes. Without that foundation, AI speed just produces more work that doesn’t land.4️⃣ Building on someone else’s platform is always riskyIncome tied to a single platform can disappear without warning. Rules change, reach drops and payments stop. Businesses that own their client relationships recover faster and adapt with less damage.5️⃣ Pivoting early saves energy and moneyWaiting rarely makes things better. The longer a broken model is protected, the more time and cash it burns. Moving sooner creates space to adjust, learn, and rebuild while you still have momentum.More resources from Anjeanette:* Her 10 Minute LinkedIn Fix* Her workshop, How to Land Clients on LinkedInIn this episode we cover:00:00 Introduction to Anjeanette Carter03:01 “Half a million… then zero” (the YouTube wipeout)07:53 The copywriting edge most founders don’t have11:24 When ChatGPT hit: panic, denial, then reality14:11 Why she laid off 7 writers (the part people dodge)19:27 The moment AI beat her team’s work21:56 “I don’t need anybody” (becoming a one-person agency)24:52 You’re not their mummy (hard lessons on leadership)29:33 How she hacked LinkedIn from zero31:38 AI won’t save you if you don’t know the game33:36 The one thing AI still lacks: judgment36:44 AI agents: promising, not ready39:13 3 LinkedIn profile fixes that pull clients in40:35 The LinkedIn lie that keeps you invisible42:12 “Lurkers are buyers” (the real conversion pattern)43:58 Viral posts vs paid posts: what actually makes money45:13 Her dad’s rule: follow the bank account47:40 Money noise (why “enough” never feels enough)48:44 The moving goalposts problem49:54 Timers, not willpower (how she moves fast)53:20 Her controversial take: SEO gets wiped first54:49 “Pivot early. Hope is a four-letter word.” Get full access to Millennial Masters at millennialmasters.net/subscribe
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    59 m
  • How to negotiate your next promotion 💰 | Yota Trom

    How to negotiate your next promotion 💰 | Yota Trom
    Dec 22 2025
    📺 Watch now on Substack or YouTube | 🎧 Listen on Spotify or Apple PodcastsThis week’s Millennial Master is Yota Trom, executive coach and promotion strategist.Yota has worked inside some of the biggest tech companies in the world. She did the long hours at Yahoo and Amazon, played the grateful employee, and stayed quiet when it came to money. And like a lot of people, she paid for it with burnout.Today, she helps founders, leaders, and high performers fix the exact problem she once had. Not by telling them to “work harder”, but by teaching them how to ask properly, position their value, use personal branding as leverage, and build a business case the company can’t ignore.She’s helped clients 3x and 4x their salaries, move from manager to VP, and stop blaming the system when the real issue was never knowing their worth.This conversation is about money, promotions, and self-belief. And why most people stay underpaid not because they’re bad at their job, but because they never learned how the game actually works.🔗 Find Yota on LinkedIn and InstagramTakeaways from Yota’s episode1️⃣ Most people are underpaid because they’ve never done the mathsA huge number of high performers have no idea what their role is worth in the market. They benchmark against friends, old salaries, or what feels “good enough,” not against data. Until you understand the real value of your skills, level, and impact, every pay conversation starts from the wrong number.2️⃣ Promotions are business decisions, not rewards for effortCompanies don’t promote people because they work hard or feel loyal. They promote when there’s a clear return. The strongest cases show how a bigger role changes outcomes for clients, revenue, team performance, or decision-making. If you can’t articulate that clearly, the answer will drift or stall.3️⃣ You’re probably already doing part of the next roleWhen people map out what they do today versus what the next level actually requires, the gap is usually smaller than they think. Many are already operating at 30-60% of the role above them without realising it. Writing this down is often the first moment they see their own leverage.4️⃣ Managers aren’t your only decision-makersMost promotions are discussed in rooms you’re not in. Senior leaders form opinions long before anything is announced. Building visibility and trust across the wider leadership group massively increases your chances, especially when managers aren’t strong advocates on their own.5️⃣ Positioning yourself is a leadership skillAs you get more senior, how you communicate your value becomes part of the job. Being clear about your strengths, impact, and direction helps others place you correctly when opportunities come up. This applies internally with leadership teams and externally through personal branding and visibility.More resources from Yota Trom:* 1:1 coaching to fast-track your next promotion* Build a standout personal brand as a founder* Download the free workbook to uncover your real value📚 Yota’s book recommendationMindset: The New Psychology of Success by Carol S. Dweck — Yota comes back to this one because it explains why so many capable people stay stuck. If you don’t believe you’re allowed to grow, ask, or take up space, no negotiation tactic will save you. This book helps you fix that at the root.In this episode we cover:00:00 Introduction to Yota Trom02:14 Stop asking for a raise, build a business case10:24 From Yahoo and Amazon to coaching full time15:40 The unsexy reason people stay underpaid16:41 The six-step promotion plan (in plain English)23:35 Your manager is not your only advocate27:31 Founders: Why your best people drift off31:17 What motivates people when money is capped35:26 Self-worth, scarcity, and founder pay guilt38:59 “Fairness” and why positioning gets rewarded44:48 Personal branding as a promotion weapon51:03 Find your “superpower” and make it obvious57:51 AI adoption: mindset is the real blocker01:02:04 Scaling yourself without burning out01:06:54 Fear, doubt, and the push that changes everything Get full access to Millennial Masters at millennialmasters.net/subscribe
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    1 h y 11 m
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