How I Failed My Startup & Tactical Advice So You Don’t Fail Yours (4 of 4)

Mike Chirokas
5 min readSep 6, 2021


Reason #4: I didn’t try to raise money.

I recently failed a startup that I worked on for over a year. It wasn’t an “I raised $5M, built a team, launched a product, and got bought for less than fair market value” failure either. I failed to raise $1, failed to build a team beyond myself, and failed to launch the product.

I failed because I didn’t try to raise money.

The five terrible reasons I didn’t try to raise money soon enough were:

  1. I thought I wasn’t ready
  2. I underestimated the amount of work it would take to get a beta
  3. I didn’t financially model out the business soon enough
  4. I didn’t know any investors
  5. I didn’t want to show anything until I was proud of it

Why I should have tried to raise money:

1. I would have built a list of investors who said, “not today, but let me know where you are in a year.”

If the first thing I did was build a deck and pitched investors, I doubt any investors would have sent a dollar my way. Still, I think a few may have been willing to join the journey on a consistent “what’s going on” business update similar to the customer board I built — putting me in a better spot when I needed to raise money later date.

2. I would have stumbled upon mentors more quickly.

When I finally began putting a pitch deck together, I had a tangible thing to ask the most intelligent people I knew to review. It was the door I used to connect to several mentors, including Matt Pru. He ended up helping mentor the business by helping me test cost per acquisition using CPC campaigns (and find out that it was going to cost a shocking ~$70/user using CPC campaigns).

3. Creating a pitch deck would have forced me to clarify the problem.

Whenever writer’s block screeches my productivity to a halt, it is almost always because I haven’t done enough research on that topic. My cure for writer’s block is doing more interviews and gathering more data. I had the same writer’s block when creating the problem slide for my pitch deck. I could tell you why I started the company and I could outline the future of autonomous finance and show how my business fit perfectly in that future, but it wasn’t easy to pick a single problem I tackling. It felt like there were too many problems it was tackling simultaneously; I needed to pick one nail and hammer it.

Drafting the pitch deck illuminated the issue and sharing it with folks for review bolded, highlighted, and capitalized that I needed to go back and do more interviews and gather more data.

4. I would have clarified a business model.

I went too far without figuring out how much APIs (i.e., Amadeus, Dwolla, Firebase, Plaid) and marketing would cost at a user level. When I finally built a pitch deck, I modeled the financials and found that the business would not become profitable until we hit more than 1,000 paying users. More importantly, I could not fund the first 999 customers from my meager savings, so I needed external funding or a business model switch.

5. I would have defined a marketing plan.

A mentor graciously reviewed my pitch deck and pointed out a gaping hole in the marketing plan. I had a remarkably vague marketing plan that included “SEO and PR.” That doesn’t cut it for a business competing with financial services and travel businesses for eyeballs and time — two of the more expensive markets to compete. Per his recommendation, I went out and asked someone who had been deep in marketing for startups for some advice and created a day one marketing plan.

6. I would have prioritized the product roadmap more tactically.

The most significant impact on the roadmap was user feedback, but another impact would have been the reasons investors rejected me. For example, if investors focused on my technical execution pace, I could have focused on launching lean and fast — without much differentiation. If the main concern was competition, I would have dug into a significant differentiator and concentrated on a vertical data strategy. If the main concern was monetization — I would have prioritized partnerships. Instead, I tried to prioritize all of those and failed to launch anything.

Tactical recommendations for trying to raise money sooner

1. Make building a pitch deck your first exercise to uncover falsifiable hypotheses.

Start by pretending that everything you are saying is correct. Maybe you know something about the space, the customers, etc. And then try to figure out if this is true or not by using user interviews, research interviews, usability tests, and surveys.

2. Ask people to review your pitch deck.

Even if you think your pitch deck sucks, get it in front of people. Having a tangible thing for someone to review asynchronously will likely lead to uncovering unknown unknowns and potentially finding mentors.

3. Create an email list where you share business updates with investors.

Creating an investor-focused business update email list is a tactical recommendation that I didn’t implement myself, so I don’t know if it will work. Still, I’ve heard of other founders doing it with some success. The upside is significant, and the downside is negligible. Bonus: you’ll show you’ve got sales skills.

4. Prospect for investors using Foundersuite

I used Foundersuite and filtered on who might be interested in this business. I only reached out to three investors the entire time I ran my business — shame on me. But, other than Andreeson Horowitz (no response… shocking…), the other two responded, and I had a casual video chat (not a pitch) with the person I found via Foundersuite. My tiny sample of 100% sounds pretty good to me!

5. Use LinkedIn to reach out to investors cold.

If you reach out on LinkedIn, it can go one of three ways: 1. they completed ignored the message. 2. they accept the connection with your message and respond. 3. they accept the connection but ignore your message — meaning you have one more investor that will see your business updates in their LinkedIn feed. I tried this method with one potential investor, and we connected for a meeting.



Mike Chirokas

I'm a marketer, developer, and tinkerer who recently failed a startup. Here to tell my story so you don't make the same mistakes I made.