Hey there Founder👋
If you're reading this, you're probably knee-deep in building something bold — something yours. Whether you're navigating your first hire, testing your MVP, or trying to figure out if ramen noodles count as a business expense (they do), just know: you’re not alone.
This week, we’ve handpicked five powerful reads — raw, real, and ridiculously helpful — to give you that edge. From navigating cash flow fears to mindset coaching with AI (yes, really), this week’s roundup is here to help you grow as a founder and as a human.
Let’s dive in ☕👇
Don’t have time → Check our TL;DR1
🧠 Rethinking How You Make Decisions
👉 How Asking Smarter Questions Leads to Better Startup Outcomes — with Dan Secretan
As a first-time founder, it can feel like every decision is a shot in the dark — which market to enter, who to hire first, whether that “maybe investor” is worth the follow-up. The instinct is often to look for more data. But what if the real answer isn’t more information… but better questions?
In this article, Dan Secretan (co-founder of Xapien) shares how powerful insights are born not from having all the answers, but from being radically curious. He built a company whose entire value is rooted in surfacing deeper understanding — and his approach to asking better questions is something every founder can steal.
For first-time founders: This is your unfair advantage. You won’t have the experience or networks others do — yet. But you can be the one who listens more deeply, questions more intelligently, and seeks to understand what others overlook.
💬 “We don’t lack information — we lack insight.”
🧠 Mindset Tip: Trade fast answers for thoughtful questions. Insight isn’t found — it’s earned.
🤖 Coaching Your Inner Founder with ChatGPT
👉 6 ChatGPT Prompts to Develop a Powerful Entrepreneur Mindset
Let’s be real — the early days of building a startup are an emotional rollercoaster. One moment you're confident and crushing it, the next you're doubting everything. Sound familiar?
This Forbes article shares six powerful prompts you can use with ChatGPT to coach your own mindset — like having a therapist, business coach, and cheerleader all in one. From navigating fear to unlocking clarity, these questions help you reset your brain when it’s spinning out.
Why it matters for first-time founders: You don’t always have mentors on speed dial. You don’t always have the time (or budget) for a mindset coach. These prompts let you pause, reflect, and grow — in real time.
✨ “Your mind is your most powerful tool. Train it.”
🧩 Founder’s Practice: Build a weekly ritual. Start Mondays with a mindset check-in using these prompts. You can’t build a great company without building the mindset to match.
⏳ The Real Startup Grind: 17,784 Hours in 5 Years
👉 How I Spent 17,784 Hours as a Startup Founder — by Maggie Hott
If you’ve ever wondered, “Am I spending my time like a real founder should?”, this article is your mirror.
Maggie Hott breaks down exactly how her time was spent over five years of running a startup. What she thought would matter vs. what actually did. How long things really take. And what she learned from the burnout, breakdowns, and breakthroughs.
Why this hits home for first-time founders: No one tells you how much time you’ll waste on the wrong things. Or how often you’ll feel pulled in 10 directions. This piece gives you permission to course-correct — before you hit the wall.
🔍 “Your calendar is a mirror. What does it say about your values?”
🧠 Mindset Shift: Time isn’t just a resource — it’s your strategy. Audit it often. Protect it fiercely.
💸 Money Matters: Staying Out of the Red
👉 How Small Businesses Can Avoid Debt in 2025
Money is one of the top stressors for first-time founders. You’re probably juggling costs, wondering if you can afford that next hire, and watching your runway like a hawk.
This guide offers a realistic look at staying financially healthy in 2025 — avoiding early debt traps, managing lean months, and building financial resilience even before revenue takes off.
Why it matters for first-time founders: When you’re new, it’s easy to overestimate what you need and underestimate what things cost. Debt feels like a shortcut, but can quickly become a trap. This article helps you stay lean, intentional, and in control.
💬 “Run your startup like you’re already bootstrapped — even if you’re not.”
📉 Founder’s Tip: Get intimate with your numbers. Cash flow doesn’t lie. Profit might not happen right away — but debt doesn’t have to, either.
⚖️ Bootstrapped vs Funded: What’s Right for You?
👉 Bootstrapped vs Funded — Which Path Should You Choose?
It’s one of the first big questions every founder faces: Do I raise money, or go it alone?
This article explores both paths — the control and creativity that comes with bootstrapping vs. the speed and resources that come with outside funding. But most importantly, it reminds you that this is a deeply personal decision.
For first-time founders: It’s easy to fall into the hype. Everyone’s talking about rounds, valuations, and unicorn dreams. But your journey doesn’t need to look like anyone else’s. You get to choose what kind of business — and life — you want to build.
🧭 “Funding can accelerate your growth — or compromise your freedom.”
💡 Mindset Check: Raise money when you’re clear on your vision, not when you’re unsure of your worth. You’re not behind — you’re just getting started.
✨ Let’s Keep Building Together
If this newsletter made you pause, reflect, or exhale — that’s the point. We’re here to help you build not just a business, but a better you in the process.
🧭 TL;DR — This Week's Mindset Nuggets
Here’s your founder fuel in 5 quick takeaways:
🧠 Deeper decisions start with better questions.
🤖 Train your mind — it's your most important co-founder.
⏳ Time is your strategy. Use it like a founder, not an employee.
💸 Financial survival = founder freedom. Protect your runway.
⚖️ Your path (funded or not) is yours to define. Own it.