Bootstrapping One Startup While Raising for Another

The Startup Funding Journey: Two Paths at Once

I'm living two startup realities at once, and they're happening in the same week. This startup funding journey has taught me more about foundership than any textbook.

On one hand, I'm applying for funding for the first time with MyAmbulex, a direct-connect NEMT platform born from 15+ years in transportation operations. On the other, I'm launching SharedTask.ai, a lightweight coordination tool I bootstrapped entirely with no investors, no team, just speed, simplicity, and a lot of late nights.

Two startups. Two completely different energies. One is about scale and storytelling. The other is about speed and execution. And somehow, both are teaching me more about what it actually means to be a founder than any podcast or framework ever could.

I didn't plan for both to hit their peak moments simultaneously. But here we are. And honestly? The contrast is clarifying everything about bootstrapping vs fundraising.

Founder Lessons from Bootstrapping (SharedTask.ai)

SharedTask.ai was born from a simple frustration: group coordination is chaos. Too many texts. Too many "who's bringing what?" messages. Too much friction for something that should be simple.

So I built a solution: Create an event, share a link, people claim their tasks in real time. No logins. No downloads. No learning curve.

Bootstrapping this project reminded me why I love building in the first place. When every line of code matters, when every UI decision is yours alone, and when every dollar counts, you focus on what actually matters: shipping, learning, improving.

Here's what bootstrapping forced me to learn (or re-learn):

Bootstrapping isn't just about saving money; it's about staying sharp. It's the difference between theory and practice. And it reminded me that sometimes the best way to validate an idea is just to build it and see if people use it.

What the Fundraising Journey Teaches You (MyAmbulex)

While SharedTask.ai was all about moving fast with bootstrapping, MyAmbulex required something different: slowing down to tell the story right for the fundraising journey.

I've spent over 15 years in transportation operations, running fleets, managing logistics, working directly with providers. The pain points weren't theoretical; they were things I dealt with daily. Disconnected systems between brokers, carriers, and vendors. Unnecessary barriers with margins squeezed by middlemen who added friction, not value.

MyAmbulex was my answer: a marketplace where healthcare facilities and transportation providers connect directly, with full transparency and fair economics.

But here's what I learned: having lived experience and operational know-how isn't enough when you're raising capital. Investors aren't just buying your resume. They're investing in your ability to articulate why now, why you, and why this will scale.

The Bootstrapping vs Fundraising Paradox

Here's the thing nobody tells you: being a founder means holding contradictions in your head at the same time.

You need the patience of a bootstrapper and the boldness of someone asking for millions. You need to move fast and think long-term. You need to be resourceful with what you have and confident in what you're building toward.

Balancing both is exhausting. In the same day, I can go from debugging an event-sharing feature to refining a financial model. From writing marketing copy to rehearsing my pitch for investors. From celebrating a new user signup to stressing over cash flow projections.

But then I remember: confidence isn't about never doubting; it's about moving forward anyway. What will I do if I don't get funded? What if SharedTask.ai doesn't hit 1,000 signups in the first 30, 60, 90, or 180 days? Then what?

My confidence can't be rooted in having all the answers. It has to stand on something deeper: the belief that in time, my strengths will prevail. I'm not pretending what I built is good; I genuinely believe it is. And while both products will need updates and corrections, the end goals are still achievable. When investors take the plunge, we'll iterate together until we find the version that's in harmony with what customers actually need and expect.

Confidence isn't knowing you'll succeed. It's deciding your strengths matter more than your doubts. I've had to narrow my focus from "100 great ideas" to two startups that actually matter. Maybe being a founder is about balancing ideas, time, resources, and focus, and trusting yourself to navigate the chaos.

What's Next in My Startup Funding Journey

Both MyAmbulex and SharedTask.ai started from the same instinct to remove friction. One removes it from medical transportation, the other from group coordination. Different industries, same obsession.

Right now, I'm in the thick of it. SharedTask.ai is live and learning from real users. MyAmbulex is in the application phase, waiting to see if the story I've told resonates with the right investors.

Both journeys are just beginning, and I have no idea how either will turn out. But building both simultaneously has taught me more about myself as a founder than playing it safe ever could.

Resourcefulness and ambition aren't opposing forces; they're complementary skills. Speed and strategy can coexist. The best way to figure out what kind of founder you are is to just keep building, keep iterating, and keep showing up.

If you're juggling multiple projects or trying to figure out whether to bootstrap or raise, I'd love to hear about it. We're all figuring this out together.