This is an inside look into my mid career left turn from a cushy tech job to entrepreneurship. It's been called "How I Built This live... but without the known glorious ending." I share the details of how I actually do this and what happens when we launch.

All Posts

Every post from the journey so far.

Show Me The Money: What we made, what we spent, and what we learned for next time

Show Me The Money: What we made, what we spent, and what we learned for next time

APRIL 16, 2025|LESSONS LEARNED

Over a couple of quarters, I bootstrapped my first software business — SnapFile — with a co-founder. We built software to help small business owners file their BOI Reports under the new Corporate Transparency Act. The product worked, people paid us, and we even had repeat customers. But by the end, we had to shut it down thanks to legal and regulatory curveballs we couldn't control.

How We Built This (With AI): Building SnapFile with AI and a Two-Person Team

How We Built This (With AI): Building SnapFile with AI and a Two-Person Team

APRIL 10, 2025|AI

When we started out building SnapFile, we were two full-time mid-career adults with some moonlighting help—and a whole lot of AI. Thanks to tools like ChatGPT, Cursor, Ideogram, and more, we were able to go from scratch to a launched product way faster than we expected.

How Not to Use Google Ads as a Small Business

How Not to Use Google Ads as a Small Business

APRIL 8, 2025|LESSONS LEARNED

We had a simple-sounding goal: reach small business owners who needed to file a new government report. We had a product, a website, and a deadline. So we fired up Google Ads, crossed our fingers, and waited for traffic to roll in.

RIP SnapFile

RIP SnapFile

APRIL 7, 2025|LESSONS LEARNED

We Built a Startup. We're Shutting it Down. Here's What Happened.

What's harder than making your product? Selling it

What's harder than making your product? Selling it

APRIL 7, 2025|LESSONS LEARNED

When I left my cushy tech job to start a business, I thought the hardest part would be building the product. I was wrong. The real challenge wasn't the product—it was convincing people to buy it.

The spam email that sparked the idea for SnapFile, our little company! Also--our launch announcement.

The spam email that sparked the idea for SnapFile, our little company! Also--our launch announcement.

JANUARY 16, 2025|BUSINESS BUILDING

Like many business owners, my inbox is often a wasteland of emails offering services I may or may not need (looking at you, LegalZoom). Most of the time, I just hit delete. But after the 5th time of seeing "Do Your BOI Report Now, only $299" I decided to Google this BOI thing.

90% of startups fail. Any guesses where our first one landed?

90% of startups fail. Any guesses where our first one landed?

DECEMBER 19, 2024|LESSONS LEARNED

When we launched SnapFile, we were prepared for the risks. What we weren't prepared for was the implosion of a little industry thanks to the judicial branch of the government. We've heard the cliché that 90% of startups fail. We knew these odds, and we took them seriously.

From Bugs to Beta (Different Bugs): My Experience With Build-Test-Iterate

From Bugs to Beta (Different Bugs): My Experience With Build-Test-Iterate

OCTOBER 27, 2024|LESSONS LEARNED

So you've got a product prototype, you've tested demand, now how do you launch it? We've all heard the concept of build-test-iterate, but what does that actually mean? And what do you actually do in each step?

Finding a cofounder: thorny topics before you commit

Finding a cofounder: thorny topics before you commit

OCTOBER 7, 2024|COFOUNDING

So you've been doing the coffee chats and have a potential cofounder. You've had the "mile marker" discussions, but before committing, you need to align on key aspects that could determine the success or failure of your partnership—topics like economic splits, funding strategies, and division of roles.

Finding a cofounder: like business dating

Finding a cofounder: like business dating

OCTOBER 6, 2024|COFOUNDING

Similar to personal life, entrepreneurship involves figuring out what your priorities are, meeting people to see if there might be a good professional fit, discussing your goals and values, and making a call if it's worth moving forward or not. It's also a bit awkward, just like in your personal life.

Entrepreneur's Guide to Logo Design: Using AI, Figma, or Outsourcing

OCTOBER 3, 2024|AI

A professional logo builds credibility and improves brand perception, even in the early stages. It's useful in landing pages, Google Ads and other platforms, inside your product prototype to make your product concept look more real, etc. But how do you make one without design skills?

How To Use AI to Build Your Business (Or Just Work Smarter)

How To Use AI to Build Your Business (Or Just Work Smarter)

OCTOBER 2, 2024|AI

By now, we've all heard about how AI will change our work lives, but the truth is, for many of us, how to use it and practical applications are a mystery. I felt the same way until I started using it daily to build my business.

Charting Your Own Course: Key Mile Markers for Considering Funding or Bootstrapping

Charting Your Own Course: Key Mile Markers for Considering Funding or Bootstrapping

OCTOBER 1, 2024|BUSINESS BUILDING

The classic startup story begins with founders, an idea, and venture capitalists just crazy enough to take a chance on an idea. But is that the only way to build a business? In this post, I'll outline some things to ask yourself as you're thinking about how you might execute on your business.

Interpreting the Tea Leaves of Google Ads Data

Interpreting the Tea Leaves of Google Ads Data

SEPTEMBER 30, 2024|MARKETING

After running a Google Ad for a week or two, you'll start gathering data that can help you understand what demand might look like for your product. But how do you read these digital tea leaves? Here's a guide to the key metrics you should focus on and what they can tell you about your product's potential.

Surviving Google Ads: A Beginner's Guide to Testing Demand (Without Losing Your Mind)

Surviving Google Ads: A Beginner's Guide to Testing Demand (Without Losing Your Mind)

SEPTEMBER 29, 2024|TOOLS

In the first few posts, we talked about finding problems, who might pay, what the business could look like, and how to test product demand with a landing page. How will people find your landing page? A Google ad!

How to test product demand before you have a product

How to test product demand before you have a product

SEPTEMBER 26, 2024|TOOLS

In the first 3 steps, we found problems, thought through propensity to pay, and have a rough business calculator. Wouldn't it be nice to know if someone wants your thing before you go to the trouble of building it? It's a great way to avoid spending a ton of time and resources on something people don't want… but how?

Step 3: Could this be a good business?

Step 3: Could this be a good business?

SEPTEMBER 25, 2024|BUSINESS BUILDING

Now that you've identified problems (step 1) and figured out who might pay for them (step 2), it's time for the fun part—turning ideas into numbers with some quick business math!

Step 2: Validating Your Business Idea—Will People Pay for It?

Step 2: Validating Your Business Idea—Will People Pay for It?

SEPTEMBER 24, 2024|LESSONS LEARNED

You've identified some problems in step 1. Great! Now, let's move on to step 2: figuring out if people will pay you to solve them.

Step 1: Solve Real Problems

Step 1: Solve Real Problems

SEPTEMBER 24, 2024|LESSONS LEARNED

Have you ever heard of companies failing due to lack of product market fit? Yea me too, it's the #1 reason companies fail. And 98% of startups fail in the first 5 years. But how do you avoid this in your own entrepreneurial journey? Start with the problem… but how? Read on.

From "Success" to Starting Over: Why I Left My Comfortable Tech Job to Try Entrepreneurship

From "Success" to Starting Over: Why I Left My Comfortable Tech Job to Try Entrepreneurship

SEPTEMBER 22, 2024|LESSONS LEARNED

From the outside, my career has been more than I could have hoped for. Growing up as a blue-collar kid in Western Colorado, I never imagined I'd reach the professional success I have. By mid-career, I'd worked at some of the world's most respected companies, built new skills, and increased my pay along the way.