Entrepreneur
I will never regret bootstrapping my business — but that doesn’t mean it was easy. Now that they’re so far in the rearview, it’s easy to look back on those early days through the rose-colored haze of memory: the up-with-the-birds mornings, the evenings where I was so enthralled in my work that dusk faded into night without my even noticing. It was exhausting, but it was also invigorating. I was building something completely mine, on my own steam.
But if I were to do it all again now, I know my journey would look completely different. Because now, I’d be using AI.
Don’t get me wrong — I actually think there’s value in having built my business the hard way. My bootstrapping journey is where I learned not just how to found a company, but how to lead one.
But would I choose to do it like that again, with all the resources of 2025 at my disposal?
Absolutely not.
Just like I don’t use a scrub board to wash my clothes or mail a letter every time I want to reach out to a friend, building a business today means using all the modern tools at your disposal — doing otherwise is simply a waste of time. Here are some of the most impactful ways AI is changing the game for bootstrappers right now.
Related: How I Use AI Tools Daily to Build Better Habits and Hold Myself Accountable
Streamline everything
When you’re bootstrapping, time isn’t just money — it’s momentum. Every hour you spend buried in spreadsheets or manually responding to emails is an hour you’re not pitching a new client or refining your product. That’s why one of the smartest moves a bootstrapped founder can make is to treat AI like a team member whose job is simple: handle the busywork so you don’t have to.
AI-powered tools can now automate entire workflows that used to eat up hours of your week. Need to log leads, send follow-ups or route a customer request to the right place? Tools like Zapier can string those tasks together into seamless workflows that run 24/7. AI assistants can draft emails, schedule meetings, transcribe calls and even analyze sentiment in customer reviews. Meanwhile, predictive analytics tools help you spot trends and make decisions based not just on intuition, but on real-time insights.
At Jotform, one practice I swear by is regularly mapping out my workflows to identify what can be automated. I’ve seen firsthand how even a few small changes — like removing redundant approval steps or auto-generating reports — can free up huge blocks of time and mental bandwidth. As a stretched-thin founder, those wins add up fast.
Related: How I Turned AI Into a Teammate, Not Just a Tool — and How You Can, Too
Level-up customer support
In the early days of my company, I found myself feeling less like an entrepreneur and more like an always-on-call customer support agent. I spent countless hours fielding questions, troubleshooting issues, and trying to keep users happy. It was rewarding in some ways, but it was also a major drain on my time and mental energy. It was only after I hired our first customer support specialist that I was finally able to redirect my focus to growing my business. But getting to that point took a long time.
Today, AI offers a better way — and you don’t need to wait until you can afford your first hire.
With AI-powered customer service tools, bootstrapped founders can build a responsive, around-the-clock support system that scales with demand. Tools like Intercom’s Fin or Zendesk’s Resolution Platform can instantly handle frequently asked questions, resolve simple issues, and even recommend products — no human input required. These aren’t the clunky, rule-based bots of the past. Modern AI agents can understand context, make decisions based on customer intent, and take follow-up actions like processing a return or suggesting a pricing tier.
Ultimately, support won’t scale itself. But AI can get you pretty close. Before customer questions start piling up — and pulling you away from your core mission — put systems in place that can handle the day-to-day, so you can stay focused on building the future of your business.
Related: 8 Ways to Use AI to Keep Your Customers Happy
Prototype faster
One of the biggest hurdles for early-stage founders is turning an idea into something real. Building your first version — what’s often called a minimum viable product, or MVP — can take months, cost thousands and eat up the very resources you’re trying to conserve. When I bootstrapped my business, this process was slow and painstaking. Every feature required custom development, and each decision felt high-stakes. But today’s AI tools have completely changed the game.
Now, you can validate an idea, test demand, and build a functioning prototype before writing a single line of code. AI-powered market research tools can help you pressure-test your idea, identify gaps in the market, and even generate early messaging and positioning. From there, you can move directly into building mode using AI-assisted no-code platforms like Bubble, Glide or Softr, which offer generative tools to create working web apps or landing pages based on simple prompts.
These tools offer more than just speed — they offer clarity. I’ve written before about how an idea without the right market is destined to remain an idea. AI can help you get products into users’ hands faster, so you can test, refine and pivot without sinking too much time on something that may not pan out. It’s the difference between building faster and building smarter, and when you’re bootstrapping, that edge can make all the difference.
Being a bootstrapped founder isn’t easy. But thanks to AI, it’s never been easier than it is now. Take advantage of the tools that are out there, and save your brain for mental heavy lifting that only you can do.
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I will never regret bootstrapping my business — but that doesn’t mean it was easy. Now that they’re so far in the rearview, it’s easy to look back on those early days through the rose-colored haze of memory: the up-with-the-birds mornings, the evenings where I was so enthralled in my work that dusk faded into night without my even noticing. It was exhausting, but it was also invigorating. I was building something completely mine, on my own steam.
But if I were to do it all again now, I know my journey would look completely different. Because now, I’d be using AI.
Don’t get me wrong — I actually think there’s value in having built my business the hard way. My bootstrapping journey is where I learned not just how to found a company, but how to lead one.
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