How I Failed My Startup & Tactical Advice So You Don’t Fail Yours (3 of 4)

Reason #3: I didn’t ask for help soon enough.

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 ask for help soon enough.

The six terrible reasons I didn’t ask for help were:

1. I didn’t know what value I could give back in exchange.
2. I thought no one cared about my business other than me.
3. I didn’t know I needed help.
4. I didn’t know what to ask.
5. I believed that because I could do it all, I should do it all.
6. I didn’t know who to ask.

Why I should have asked for help earlier:

1. I would have gotten better at communicating the value of the startup.

I loved talking about my startup. Nothing made me happier than sharing what I was building, why I was building it, and how the process was going. But I feared boring the folks around me, so I tried to say less. Keeping the message to myself was a terrible approach because the more people you speak to about your business, the better you get at it. If you have been around talented individuals for an extended period in the workplace, track, field, etc., you start to hear the same stories. It is because the storyteller has sharpened those stories a thousand times over. Often, we remember those stories not for their content but because of how well the storyteller tells them. Had I asked for help earlier, I would have had hundreds more opportunities to explain what I was working on to new people; people way smarter than me. I would have had hundreds of opportunities to sharpen the story, even if they had no interest in lending a hand.

For example, when I finally began to ask people for help, they would ask me to tell them more about my startup. By going through this with a dozen people, I found that when I started with why I was building an app to help more people travel more, I got heads nodding in agreement far quicker than when I began talking about what I was building and the vision for the product.

2. I would have uncovered unknown unknowns.

One of the significant challenges I had in asking for help was that often I didn’t know what to ask. Opportunities and monstrous obstacles were lying in the brush ahead of me, but because I was not an expert in every portion of the business, I couldn’t spot them on my own.

For example, it wasn’t until I chatted with a growth marketing expert that I realized I could leverage my contacts to uncover more free ad credits to test out the CPA of social ads. From spending more than $500 in ad credits, I learned that my CPA would be closer to $70 — driving a massive shift in my business model and I learned that video content would be essential — driving a shift in my marketing priorities for launch.

3. I would have built more investor relationships.

If you ask for money, you get advice; if you ask for advice, you get money. I didn’t talk to investors, so I got neither advice nor money — shame on me.

If I reached out to fintech investors in the Boston area asking for help, they would have been able to tell me tales of why the last six fintech apps that came across their desk failed. I could have used these to improve my prioritization and start with a strong pitch deck when the time came.

4. I would have prioritized finding a co-founder, spent more time prototyping, asked for help more, and tried to raise money sooner.

The four reasons I failed are likely the same reason thousands of startups have died as well, and advice-givers could have helped me prioritize goals that aligned with those needs.

For example, a mentor I respect immensely gave me the advice to find a co-founder when I first started. I was naive and recklessly optimistic and forged ahead without one, but I like to think that had three others told me the same thing, even an incredibly naive past version of myself would have implemented the advice.

Tactical recommendations for asking for help:

1. Have an answer for, “Let me know if there’s anything I can do to help.”

For me, it was my customer board. Once I started answering, “would you mind signing up for my customer board?”. My customer board email list in Mailchimp was integral in driving continuous user feedback on an ongoing basis.

2. When people offer help: take it.

I met with Matt Pru from Stackmatix once in mid-2020 and got some precious advice, especially on positioning the business. But then I went dark. A year later, when we reconnected, I realized that I had missed twelve months of growth marketing expertise. When a mentor poked holes in my marketing plan, I had Matt rescue me with a plan to answer investor’s marketing plan questions with statistics.

3. Save everyone time, get a Calendly.

Remove friction from scheduling the advice meeting by politely sharing your calendar link and letting folks find the perfect time for them. Everyone wins. I have Calendly pro, so I create one-off meetings and feel confident posting the link directly to forums like IndieHackers and Reddit when I ask for help.

4. Feel confident that many people want to help for the sake of it.

One of the main reasons I didn’t ask for help soon enough was that I wasn’t sure how to help others in return. It turns out that more people than you think enjoy helping others: I certainly do. The key is that you feed the karma machine, so please do if you have something to give back.

For example, Ross Kline helped me think through the personal side of my application and then joined my customer board. He launched an impressive podcast six months later, and I was happy to listen and give feedback on his first podcast episode.

5. If you don’t know what to ask for, ask for stories.

For example, I was trying to learn more about the travel fintech space. I knew I could learn from someone who had started this type of business before, but I wasn’t sure what to ask, so I asked her to share her story. The 30-minutes we spent chatting were immensely helpful. I learned of an entire group of competitors I had never heard of, I learned about profitable business models I hadn’t considered, and I learned that I should consider benchmarking my user experience against bucket list platforms in addition to the fintech and travel apps I was already benchmarking.

5. Reach out on LinkedIn.

Asking for help via email works, but I had slightly more success reaching out on LinkedIn. I hypothesize I had more success this way because the other person can immediately dig into more context about your history and see your face (which helps humanize you vs. email) without much effort.

For example, I was meeting with Red Ventures to discuss a credit card affiliate partnership. I wanted to go into the meeting as less of a complete newbie, so I found a former Red Ventures employee and reached out to get a bit smarter in the affiliate space. As a result, I went into the meeting with much more experience and looked much more professional.

6. Get comfortable being a “poster” instead of a “lurker” on social media and forums.

For many of us, this one is tough. But there are kind souls out there willing to help if they know you need it. When I finally started doing much more in-depth user research, I posted to IndieHackers seeking folks who saved for travel. Alec responded to my request and then offered experience and advice every week for the next six months. Alec’s advice was a significant reason I was able to push the app as far as I did. We recorded a few of our lengthy chats here.

7. Join Lunchclub.

Lunchclub is a website that pairs you with relevant people for 45-minute 1:1 video chats. It ended up being a game-changer for me by helping get me out of my bubble, being a catalyst for advice I didn’t know I needed, and helping me explore new perspectives on my business. I met over sixty fantastic people that ended up helping me beyond my wildest dreams.

For example, Lunchclub set me up with Jeff, who offered to review my pitch deck, then went way beyond the call of duty to poke holes in it, became active on the customer board, and proactively followed up. It also connected me with Eugena, who helped refine my value proposition and improve how I pitched the company via video to Mass Challenge.

8. Ask me to help you.

My goal is to use my experience to make sure you don’t make the same mistakes and thrive. So many people gave their time to help me, so please help me give back and feed the karma machine. You can find me on LinkedIn; I’m the only Mike Chirokas.