The 30-Day, Idea-To-Production Enterprise-SaaS Challenge

Can one 58-year-old, out-of-step hacker crank out an entire enterprise-grade SaaS in just a single month, with the help of ChatGPT?

In November, 2023, I’d successfully built one of the most technically complex and operationally capable projects of my career as an engineering/product leader, at a Silicon Valley fintech startup. Thanks to the immense efforts of a team of 17 developers, designers, product managers, and QA engineers that I painstakingly assembled over the course of 2 years and 8 months, Sydecar launched three enterprise SaaS products, and was faithfully moving $1B in investor capital on the platform.

By December, I was gone.

In any venture-funded startup, the capricious nature of the board and first-time founders can mean that one moment, they’re complimenting you on all the stellar feedback the product has garnered, and the next (to the time-honored refrains of “you don’t scale well enough” or “you’re not accountable enough”), it's welcome back to job-search mode!

I’ve been in this position before. Being a “0-1 guy”, I'm used to starting from no existing team, and founder hand-waves and rough sketches. I’ve repeatedly built the strong foundations of successful, long-term products, only to “age out” as the venture gets more corporate. But– and this is a big “but”– the 0-1 process usually involves years of discovery, planning, team building and management (not to mention the actual product building). And because I need to focus on all the leadership tasks, I hire smart developers to code. That means my coding skills get... rusty.

Enterprise SaaS products are complicated, and the bar for solid, fault-free systems is extremely high.

Behold the Indie-hackers!

Around the same month I got kicked off the fintech island, a colleague introduced me to the exploits of such indie-hackers as Pieter Levels, John Rush, and Alexander Isora. These guys have hit upon a method of building multiple successful, one-person ventures using:

• scrappy coding (not enterprise grade!)
• guerrilla marketing
• zero marketing spend

Sure, I can claim I’ve walked this “founder's path” before... But never at their breakneck speed, and never alone. Their approach of “listen, learn, respond, repeat” is executed in a timeline of weeks–  not months, or worse, years. Because of this speed, they:

• Don’t build any “real stuff” until they have at least a few subs or signups validating the idea, because they are confident they can build the "production solution" super quick.
• Can afford to be very public about their failures and successes as they go. Since they move so fast, building IP or "moats" becomes less critical.
• Don't bother seeking investors. Who wants to write a big check for a single month's work?
• Don’t give a damn about notching “J-shaped exits”. Any traction is a win, because they launch cheap. And they tend to launch a lot.

Some cynics think these guys faked their success claims, are just bitter about the venture funding game, or else just got extremely lucky.  All I know is, you can't fake paying for a billboard in Times Square out of your own pocket, unless something is selling like hotcakes.

Sure, but isn't Enterprise-Grade SaaS different?

For me, the enterprise product discovery/sales process has always been a sort of torture. As an engineer, there's nothing I hate more than demoing my team's product and then (inevitably) something breaks, and the subsequent hand-wave over that thing that is really just half built.

I really don't want to waste anybody's time shilling vaporware. The customer's business is relying on my service. My service has got to be real. So, invariably, I spend 6 months building a fully working product to prepare for any prospect calls.

Even after that slog, I dread prospects' feedback. Responses such as:

• "Looks neat, but it really needs to do something your product doesn't have."
• "Great job... but doesn't <insert-random-VC-funded-brand-here> already do that?"
• "Seems impressive!... but, well, switching costs would kill us... next year maybe?"

Can applying the indie-hackers credo to enterprise SaaS help out here? That is, can we follow the indie-hacker mantra, and build + sell a real product in a month? On the face of it, there's little precedent for it:

• All the indie-hackers build consumer apps, or extremely niche tools to sell to other founders. By design they solve just one small problem at a time. ("Enterprise-grade" SaaS tends to solve a lot of problems with many features.)
• Indie-hacker SaaS offerings can be slightly broken or be sorely lacking in features. Their goal: validate and then build insanely quick. Move fast and ship total s***? Again, NSFW (this won't fly in enterprise SaaS).

Regardless, how could any one individual build something truly “enterprise-grade” in as little as four weeks? Didn't I just prove it took two years to mature the Sydecar products?

The 4-Week Enterprise-Grade Challenge

Enter ChatGPT.  For the past year or so, of course, it’s been in every water cooler conversation, the next crypto-ish hotness you “shoulda gotten in early on”, etc. But in my day-to-day slog on the fintech startup, it remained in the wings. Even when my team of senior coders started to use Github CoPilot, ChatGPT really wasn’t considered to be the “innovation that ends our careers”.  My engineers still felt themselves to be the primary resource in building software products, not AI.

After the fintech decapitation, I had a thought: could I pull off a Pieter Levels 12 startups in 12 months-type challenge, using an AI coder but no human team? Are these endless TechCrunch stories and YouTubes about the uber-powerful AI's anything close to the truth?  

Just two years ago, building solid enterprise architecture, scalable systems, the latest code and UX, yadda yadda, required at a minimum 2-3 senior engineers, a designer, a PM, maybe throw in some QA automation, and... well, 6-12 months.

But now (with AI's help), could I actually build and start selling, in 4 weeks, a real enterprise-grade product ?

In February 2024, this aging hacker set out to prove he could do just that.

I decided to try and fill a systems gap I'd struggled with at the fintech, and that I couldn’t find a great solution for: serving easy, flexible, in-app user-alerts.  In an enterprise application, there are times when you must tell active users something really important. (And be positive they got the message.) These are things like unexpected service outages, pending deadline affecting a customer, or even scheduled maintenance.

I set to work making ChatGPT build a solution. After a couple attempts at crafting a good product prompt for the AI, I got ChatGPT to architect, explain, and then code up a fully working prototype in two days. That was pretty incredible.  So I immediately stuck a raft of Post-its to my wall of items I wanted this service to offer, and got into a build rhythm... targeting a live launch of the full product, in just 30 days.

Every day, I turned to ChatGPT Plus to either help me code, or flat-out write the full code on its own, for each Post-it item, which I then satisfyingly ripped off the wall, “done”.  Together, "we" built a fully operational dashboard with team access, two modern SDKs and a solid REST API.

It wasn’t always a party. ChatGPT sometimes rabbit-holed, looped back around to previous suggestions that didn’t work,  created absolutely awful icons, graphics, and dashboard layouts, or wrote plain bad marketing copy.

But when it came to actually coding, it was spot-on, 95% of the time. It was exactly like having an infinitely-patient, boundlessly energetic senior developer sitting right next to me, all day.  

I felt like the guy in the movie Limitless, who takes a drug to access all his synapses. I felt –  supercharged!

So... Did I Win the Challenge?

Well, no. I didn’t make the one month challenge deadline. I sank precious days on some features I shouldn’t have built, because the AI made it so damn easy. (ChatGPT can’t stop you from bad judgment calls!)

I wasted a frustrating week and a half adding things like “enterprise auth & team support” and even more time building a React SDK, when it’s not clear yet whether enterprises would “value the value prop” in the first place. I built an enterprise grade API and docs, when again, I don’t know if customers would ask for it (they usually, but only eventually, do, in my experience).

Despite this, I can state with authority that, at the end of just two months, I had 95% of my dream user-alerting system built and live.  (You can try it out without registering at This Is Not A Drill! Homepage.)

Product Building Got A Lot Faster.  So What?

AI or no AI, you still need to do your homework.

The hardest part still lies ahead: getting people to find my service, try it out, and buy it. Pieter Level’s advice is:  Never give anything away for free. Unless people are clicking the Buy button, you don’t have a business. 

But an AI cannot help you reach an audience of real buyers. When I asked ChatGPT for wisdom, it just told me to pay for ads on Adsense or LinkedIn,  get TechCrunch coverage, or magically create a 5 year tweet history with 50,000 followers. Yeah, good luck with that!

On top of this, my original target audience, web developers (an audience whose needs I know in depth and who I was convinced didn’t need more discovery), may never have been the buyers. It may be that product managers are the right purchasers, and I've learned they already have a choice of multiple incumbents offering as a single feature, what my service does as a whole. 

This is my bad; this is plain old Product Discovery 101. To misquote Jurassic Park, “just because you can build it (super-fast) doesn’t mean you should build it”.  In fact, running my idea this afternoon through FounderPal’s startup idea analyzer (another AI) resulted in a fortune cookie greeting: Sorry, your concept is a pretty lousy idea to try to bring to market.  (Aw heck, what does an AI know after all?!)

Is this all bad news?

All that being said, things aren't as bleak as they sound. 

I have proven to myself that myself, alone can build a certain class of business solutions in record time.  If another problem comes to my attention begging for an enterprise SaaS solution, I am confident I can build "all the things" a lot faster now, as I have all the fundamental building blocks of pretty much any enterprise SaaS.

(In the spirit of the indie-hackers, I will be sharing via this blog, all these Lego bricks, along with what I’ve learned about how to get the most out of ChatGPT, to any old hacker who asks. Or take a look at the Github.)

Assuming I truly adopt the indie-hacker approach of “fake something up, and get signups / paid subs to validate”, I’m now confident I can actually build a real solution to deliver to those customers in a month, without those embarrassing “it always breaks during a demo!” or “it’ll be ready soon, I promise!” moments keeping me up at night.

If you are, like me, concerned about Silicon Valley ageism or “successful exit-ism” shutting down your career... if you are feeling a bit like rotten horse-meat out in this brutal job market,  consider this rinse-and-repeat formula:

1. Use AI to put together, in 2-3 days, enough of a working prototype that you can create a walk-through video.
2. Feature the video (or just your value-prop), on a landing page cranked out on Umso or UnicornPlatform, to gather signups and/or paid subs.  You may not see many visitors to your new marketing site, just because, unlike the famous indie-hackers, you don’t have enough of an audience yet (I certainly didn't). But even 1 or 2 interested strangers is good enough to consider burning a month building (I’ve gotten about 4).
3. As soon as you feel there’s enough positive interest, congrats! You can go do the full build of a real enterprise SaaS. (You can, because you have the AI.)
4. 30 days later, announce (via channels covered elsewhere by many other indie-hackers) your product is now fully open for business. 
   1. Guess what? No more painful sales-masquerading-as-discovery calls with a smoke-and-mirrors product. You have a real product to sell, actually!
5. If sales are “meh” or zero, take some steps for SEO growth, and move to the next product.

The Future's So Bright, I Gotta Wear (Enterprise-Grade) Shades?

Right now, and for the next 1-2 years, I truly believe the opportunity to experiment in building solopreneur-owned, enterprise-grade SaaS products has never been greater, or more democratic.   AI may get busted for being dangerous, breaking copyrights, or just devolving into anodyne drivel, but as a tool for accelerated builders, it's a step change.

Assuming you (and I) can also master the discovery process (step 2), you have a route to successful solo enterprise startups, a route that is truly new. 

I was shocked to read that 67% of folks who know about AI don't leverage it every day. That seems crazy to me. You can build your future (and create your own exits) like never before. And if you are trying some variation of the formula I mention above, reach out and let me know what's working (and what isn't), and where the AI helps or hinders. I'd love to meet many more "enterprise-grade indie-hackers"! We can help each out.

Additional Resources To Be Aware Of (as of June 2024)

On top of using the AI's for coding, you can :

1. Launch services on top of ultra-cheap, yet super solid infrastructure like Railway and Clerk.
2. Build pretty damn good marketing sites for next-to-nothing on Umso and UnicornPlatform.
3. Create a marketing video for $39 with Paracast.io (I'm going to be testing this one).
4. If you have an API, use docusaurus for documentation that you can auto-deploy to Netlify at a total cost of $0/mo. Then, you can add Algolia search for free by just enablishing the Algolia extension in docusaurus.config.js This will give you "ctrl-k" search functionality for that professional feel.
5. Reach prospects on Reddit r/SaaS just by being helpful and spreading that oldster knowledge around. 
6. Leverage new business networks like Alignable that offer less spammy ways to network with potential clients and resellers than LinkedIn.

As I continue this journey I intend to share every resource that's helped me. If I've missed more good resources, please share!

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