27 raw lessons from my 1st year out of corporate
Last Thursday marked the one-year anniversary of me quitting corporate to build StealthX.
12 months ago, I stepped out of a comfortable role and into the unknown with nothing but a vision and a bet on myself. It’s been a year full of wins, lessons, a few late nights, and unexpected momentum. I shared a short reflection on LinkedIn to mark the milestone, and it picked up a surprising amount of engagement. That told me something… a lot of you are either building something or thinking about it.
So I figured I’d elaborate in this newsletter. Not just on what I’ve learned, but how you can apply it to your own journey, whether you're a founder, operator, or just rethinking what “work” should mean.
First, a few stats for the year
In the spirit of building in public, I thought I’d share a few stats. It’s wild to look at these after a year of focusing on the discipline of being consistent. Although not huge numbers - I’m most proud of the quality that these numbers represent.
Worked with 13 amazing clients on 17 different projects
Co-hosted 3 Product Jams and 3 quarterly executive dinners
Shipped a newsletter every week for a year (this is #52! 🎉) and grew to 276 subscribers
Hit publish on 56 podcast episodes and grew to 57 YouTube subscribers
Grew the team to 4 employees and worked with 7 contractors
Grew from 3000 to 4228 followers on LinkedIn
1. Juggling cashflow is the most stressful part
Forget the pitch decks and product strategy slides. The real stomach-drop moments come from managing cashflow. Watching invoices sit unpaid, payroll dates inch closer, or projects get delayed by a week too long. It tests your resilience and clarity like nothing else. You quickly learn that managing your mindset around money is just as important as managing the money itself.
Putting this into action: Set clear payment terms and follow up repeatedly, even if it feels awkward. Forecast out 3 months of cashflow at all times. Treat sales like oxygen, not a side task.
2. AI is second nature now
It’s not an edge anymore. It’s table stakes. From research to brainstorming to actual builds, I use AI daily in ways that free me up to focus on clients and strategy. I honestly can’t imagine running StealthX without it. It’s become part of how I think, not just a tool I use.
Putting this into action: Map your weekly work and spot tasks you can AI-accelerate. Set up smart automations and agents for repeated tasks. Learn how to prompt well. Start treating AI as a teammate/collaborator, not a novelty.
3. Bootstrapping? Start with services
Services fund your learning curve. They generate cash while you test positioning, messaging, and client needs. Products and codified service offerings can come later, after you’ve earned trust, figured out the patterns, and have actual pain points to solve. This path isn’t as glamorous, but it’s real. And it creates sustainability fast.
Putting this into action: Pick a narrow problem you can solve today. Ship work that creates clear value. Use delivery as a way to learn. Let momentum guide your eventual product bets.
4. Building a practice at a bigger firm was my cheat code
My years in consulting before StealthX were a front-row seat to what breaks inside organizations. I saw politics stall great ideas, bad hiring hurt teams, and lack of clarity crush otherwise solid strategies. That experience helped me skip a lot of rookie mistakes. I already knew where the bodies were buried. And I came into StealthX with my eyes wide open.
Putting this into action: While you’re inside a larger org, treat it like an MBA. Pay attention to incentives, power dynamics, and failure patterns. Use your role to de-risk your future build. Take notes. They’ll become your playbook.
5. Don’t skimp on tools
In the early days, it’s tempting to go cheap. But clunky systems slow you down and create friction where there should be flow. I’ve spent more on the right tools than I expected, and I’d do it again. Good software extends your capacity. Bad software burns your time.
Putting this into action: Identify bottlenecks in your daily workflows. Spend where you’ll save time or improve output. Don’t overbuy, but don’t underinvest either. Think of tools as teammates.
6. Authenticity wins
Clients can tell when you're performing. The moments I leaned into what made me different, weird ideas, spicy opinions, cheeky videos, that’s when connection happened. People want real. Not polished. The more I dropped the script, the more momentum we’ve gained.
Putting this into action: Show your work. Share your process. Talk like a human. Be clear. Cut the BS.
7. Close the laptop. Your kid’s bedtime matters more
It’s easy to fall into the trap of “just one more email.” But nothing you do in business is more important than showing up for your people. Especially your kids. Those moments don’t come back. And being present makes you better at everything else.
Right around when I started StealthX we started doing weekly family game nights on Mondays and play card/board games together. We also make it a priority to eat dinner together and do a round robin exercise we call “High, Low, Woah, Grow.” Essentially each person shares their high and low for the day as well as one thing that helped them grow and made them say “woah.” I love those conversations ❤️
Putting this into action: Block family time on your calendar. Turn notifications off. Say no to late meetings. Build a business that fits your life, not the other way around.
8. Hire doers. Not professional managers
You don’t need someone to “drive alignment” when the house is still being built. You need builders. People who can jump in, figure it out, and move. The wrong hire early can stall you more than doing it solo. Execution is the whole game.
Putting this into action: Prioritize people with proof of grit. Ask about what they’ve shipped. Look for momentum over pedigree. Keep teams small and sharp.
9. Be ruthless with your time
If you don’t protect your calendar, it will get eaten alive. Every minute you say yes to the wrong thing, you say no to something that actually matters. Being available doesn’t scale. You have to be strategic about your attention. It’s your most finite asset.
Putting this into action: Audit your week. Eliminate or automate low-leverage tasks. Schedule deep work blocks. Use a calendar guardrail if you need to.
10. Burn the ships
There’s a mental shift that happens when there’s no plan B. It forces resourcefulness. It sharpens your instincts. You stop hedging. You start creating with urgency.
This doesn’t mean burn bridges, it means to push yourself to jump before you feel ready. Bet on yourself.
Putting this into action: Go public with your commitment. Make it real. Build constraints that push you forward. You’ll be amazed what you can do when you have to.
11. Say what you actually think
It’s easy to couch things in “safe” language, especially in corporate. But people are drawn to clarity and honesty. Even when it’s sharp. Especially when it’s sharp.
Putting this into action: Don’t polish your personality out of your messaging. Use your real voice. Speak like you do off the mic. Let people opt in or out.
12. Referrals > marketing hacks
We’ve tried a few growth experiments. Nothing beats delivering great work and being referable. Clients talk. Good work travels. And trust converts faster than any funnel.
That said, having a defined marketing strategy drives a ton of clarity on where to focus energy. Spend ample time thinking through how you plan to talk about your company and what channels to invest in.
Putting this into action: Make the ask. Stay top of mind with past clients. Create things that people can easily share to show your value. Let relationships do the heavy lifting.
13. Sweat the small stuff
Little things add up. Remembering a kid’s name, paying for dinner, sending a handwritten note, these things create connection. They don’t scale. But they stick. And they compound over time. A former client of mine said it best: “Focus on decades, not deals.”
Putting this into action: Be observant. Practice generosity. Invest in moments, not just metrics. Relationships are built in the margins.
14. People will leave
Contractors move on. Partners pivot. Clients churn. It’s not personal. It’s part of the game. Don’t take it personally.
Putting this into action: Build systems, not silos. Document process. Have backups. Leave doors open.
15. Loop your kids into the process
Mine ask questions about meetings. They pitch ideas. They’re curious. And they get to see what building something looks like. Wins, stress, all of it. I’ve been surprised by the insights they share when I show behind the curtain.
Putting this into action: Talk about your work at the dinner table. Ask for their input. Let them help with low-stakes stuff. Model ownership.
16. Work out
This isn’t optional. Your brain works better when your body does too. You need endurance, not just strategy. And a 30-minute workout often saves you three hours of sluggishness. I’ve put this off for years because I felt like I didn’t have time. Now that it’s a priority and a habit, I can’t imagine not doing it. I feel soooo much better.
Putting this into action: Pick something sustainable. Schedule it like a meeting. Don’t overcomplicate it. Just move.
17. Don’t play scared
Fear makes your world smaller. It whispers worst-case scenarios and stalls your momentum. But the upside comes when you’re bold. Confidence compounds too. You just have to start.
Putting this into action: Identify where you’re hesitating. Make a small aggressive move. Reframe risk as learning. Act like it’s going to work.
18. Make the foundational decisions early
Tech debt, process debt, culture debt, they all show up if you avoid the hard conversations. Structure is freedom. The earlier you set your values and workflows, the easier everything gets. Avoiding decisions now just guarantees pain later.
Putting this into action: Write down your principles. Define your process. Revisit them monthly. Don’t wait until it’s messy.
19. When everyone zigs, zag. But zag early
Playing contrarian for its own sake is useless. But real differentiation comes from being early, not just different. And sometimes, when the zag gets crowded, it’s smart to zig again. Timing matters. So does awareness.
Putting this into action: Study where the crowd is going. Decide whether it’s signal or noise. Build from your own convictions. Pivot when needed, not when it’s safe.
20. Always create value
Even if you don’t see the ROI yet. Show up. Be helpful. Teach what you know. It all comes back.
Putting this into action: Share your frameworks. Give feedback. Support peers. Make deposits into the relationship bank.
21. Get your hands dirty
Delegation is great once you know the job. But early on, you need context. You need to feel the friction. That’s how you make it better.
Putting this into action: Do it once yourself. Learn the tools. Build the thing. Then scale it.
22. Be present
I’ve had people mention how much it meant that I responded. That the founder cared. That matters. Presence is leverage.
Putting this into action: Don’t outsource relationships. Be reachable. Follow up. Make people feel seen.
23. Have hobbies. Keep your friends
Burnout is real. And isolation is quiet. You need joy. You need community. Hustle is a means, not a lifestyle.
Putting this into action: Block social time. Prioritize things that have nothing to do with business. Stay human. You’ll build better because of it.
24. Celebrate the small wins
There are no company-wide Slack threads cheering you on. So you have to be your own hype squad. Recognize progress. Enjoy it. Then get back to it.
Putting this into action: Keep a “done” list. Treat milestones like events. Pause to appreciate how far you’ve come. It fuels the next push.
25. Don’t cheap out on the tea
The small comforts matter. They make the day feel less like a grind. A good cup of tea can change the vibe of your whole afternoon. Don’t underestimate the little rituals. They help you feel human.
Putting this into action: Find your non-negotiables. Upgrade the small stuff. Create a workspace you like being in. Enjoy the ride.
26. Choose depth over networking fluff
Coworking happy hours are fine. But most of the time, they’re surface-level chatter and performative small talk. The real magic happens over a meal with someone who’s taken the hits, made the mistakes, and still shows up. That’s where you get clarity, perspective, and connection that actually moves the needle. Less volume. More substance.
Putting this into action: Make time for 1:1s with builders you respect. Trade war stories over dinner, not drinks. Seek conversations with people who’ve earned their insights. Your network should challenge you, not just cheer you on.
27. Think twice before outsourcing for cheap
Virtual assistants and low-cost help seem appealing at first. But if you have to spend hours explaining context, correcting mistakes, and reviewing output, it’s not actually saving you time. In the age of AI, many of those tasks can be automated or handled with way less friction. High-leverage support should amplify your work, not create more of it. Cheap is expensive when it slows you down.
Putting this into action: Audit what you actually need help with. Use AI agents or workflows for repeatable, logic-based tasks. When you do hire, invest in people who understand your space and can run with minimal hand-holding. Quality pays off.
Final thoughts
Grateful doesn’t begin to cover it. This past year stretched me in every direction. It taught me how to lead without a safety net, how to create without overthinking, and how to stay grounded when everything feels uncertain. I’m especially thankful for my wife Jordyn and our two kids, who backed the vision before it was real. I’m also deeply grateful for the clients who took a chance, the team who’s helped build this thing, and everyone who believed when it was still just an idea in an Apple note on my iPhone.
Onward & upward 🤘
Drew
P.s. If you’ve never seen our anti-consultant videos, we shot a handful last December to poke fun at the clichés and make the point that we're pretty atypical. You can check them out over on our YouTube playlist.
P.p.s. I’ll be speaking at the next AI Innovation Council: Vibe Coding in Action event in Charlotte on June 23. I’ll show how I use AI to rapidly prototype apps, workflows, and client solutions. It’s live. It’s interactive. You’ll see real tools in action. RSVP here.
