Selling Investors a Ticket to Ride

What is one ride that every carnival has? The one that stands out from miles away in the night’s sky, with glimmering lights and fun sounds? The last hint is that the first one was built in Chicago, IL.

My company is slowly running out of money again. It is the ongoing struggle of starting a startup when the incoming revenue does not meet or even exceed the outgoing expenses. This situation, unfortunately, means that it is time to raise money yet again. 

I had a conversation with my co-founder about how I could raise better, or faster this time around. For context, I tried to raise this round of $500k back in January. The result was a significant amount of interest and intrigue, but little conversion to investment dollars. Since then, I have been racking my brain about why I was not able to raise. I have analyzed, and microanalyzer each part of my pitch, about my product, my financials, and market size, and have been coming up with no apparent weak spot. My co-founder said that the pitch is fine, “you have improved greatly in the pitch, but I still have not seen you put effort into getting comfortable with the numbers.” 

The numbers, there were a lot of them. The financial figures in the deck, what did they all mean, how were they going to work as we scale, unit metrics, and all. Then there are the other numbers, the investment and the ROI. On calls I had with potential investors, I would lean on my co-founder to answer those questions because he had a background in finance. But now he is saying it is my turn, “you are the CEO, if the investors can’t believe in you talking about the numbers then they will not feel comfortable placing their money in your pocket.” Well, that does makes sense, but where to start.

After thinking about this problem for a while, this week, I finally made a plan and started to take action.

Goal: To be able to confidently walk through the numbers in the model and the investment opportunity with an investor

Action Items

  • Read books investor book and angel book
  • Write out a script and scenarios of ROI 
  • Find someone in the VC community to grill me for an hour a week for five weeks

This week I started attacking the investor books. I am a visual learner, so when I read, I often draw diagrams or write notes while reading. After 162 pages into the VC handbook, I finally understood their perspective and investment. Investors want to get in early on the ground floor, ride the ride for the ups and downs and all-around a then get off at the top. It hit me; it’s just like a Ferris Wheel.

This concept may be simple and understood by most, but for me, everything finally clicked. I get it now, and I get what my job is; to sell investors a ticket to ride the Ferris Wheel. Among all the other rides at the carnival who claim to get as high as the Ferris Wheel, none do. I need to position my startup as the company that stands out from the rest and goes the highest.

Feeling Down on my Luck

It is February 11th at 11:53pm and I just finished an hour and a half weight lifting session alone in the gym in my building. Oh and today was Monday, the start to another week for most people, for others it is just another day from the continuous grind of the last weeks of days.

A Letter to Ernesto

Dear Ernesto,

It’s not you, it’s me. It must be me the crazy one right. It’s like this fine line of crazy or brilliance. Some say there is overlap between the two while others see it more black and white. Regardless what’s it matter, you have ruled me crazy and that means our conversation is over (for now).

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Living in the valley of death with the end zone in sight

“You’re on the 10-yard line.” The man said, sitting across from me at the Starbucks in Kenosha, Wisconsin. After many coffees with other executives, I have learned to just listen when they talk because they typically have more experience and insight than I have. Plus interrupting mid thought is never a good idea, so I just sat there nodding my head from time to time and opened my ears. The man continued, “I don’t mean to be harsh, but just giving you my honest read of your situation. You should be proud because you have completed 90 yards, but you are stuck on the 10-yard line. This is the place where so many startups land and hover until their next move. Take it or leave it, but a word of advice is to consider your next move carefully as it will be predictive of your startup’s success.” It took me a few minutes to fully grasp what he was saying. Were we in a good place? Heading down the right direction? Or completely off base? At this point, I was intrigued partly because this was only our 3rd time interacting since I first sent him a cold email and because he spoke with such clarity and understanding on where my startup was and where we were going. As he continued to talk, I started to comprehend what he was saying. The man was laying out the options of how to move the company forward and how he could help.

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The Missing Piece in Finding Product/Market Fit

I haven’t written for a long while, well actually just haven’t published. I have written a few pieces and notes about my journey, but they have been stuck in a draft mode. No doubt they are good pieces about how the startup life has been going and the challenges I have been facing, but finishing them off till perfection (or a point where they are better than they are) has not yet happened.

It is somewhat indicative of where I am today with the company and why I decided to publish this piece. Over the past few weeks, I have been reading a few famous essays from Paul Graham and Marc Andreessen. I have never been one for long articles or essays, but have actually gained some perspective and value from these. The one that has been stuck in my head which relates so heavily to today is The Only Thing that Matters. In short, this essay is about understanding and analyzing three essential elements of a startup (team, product, and market) and their contribution to the success or failure of the startup. It ends with pointing out that the product/market fit matters most. Regardless of the great or lousy team or the good enough or perfect product, at the end of the day the market wins, the market decides if your product is a fit for its needs and desires.

This idea has been revolving in my head since I read this article a few days ago. More

What is traction?

I’ve been doing a lot of information gathering lately. Talking to entrepreneurs who have sold their companies, talking to investors from angels to venture capitalists and talking to advisers. From every conversation, I have come away with 1 consistent word: traction. When I dug further that term seemed to fall apart into a million different pieces. Some said traction was having a million dollars in recurring revenue each month, others said traction was having letters of intent and contracts signed and others said traction was having 1000 of your first products in the hands of customers.

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Hardware is Not Hard, Healthcare Is

For the longest time, I thought that building hardware was hard. Coming from a software background with little exposure to engineering or hardware, I thought the odds were stacked against me to build a hardware startup. The age-old advice in entrepreneurship always struck a core with me that said, “stick to what you are good at.” I was clearly not set up to succeed from the beginning.

In college at Indiana University (IU), I studied informatics with a focus in business. For those of you who don’t know what informatics is, it’s the application of technology to different disciplines; basically, the idea that there are all of these computer science folks out there and business people and they don’t know how to talk to each other. Coming out of informatics I was given the toolset to be able to program as well as translate requirements from one side to another. The other thing to consider from my time at IU was that at the time they didn’t have any engineering programs beyond computer science. If you wanted to do engineering you went to Purdue up north, and for everything else, you went to IU. This also meant that there wasn’t a community of people familiar with hardware projects in Bloomington, IN which added to my misfortune. More

Startup = Start + Up

Fridays are supposed to be good days, right? Well this morning was a great day, but this afternoon not so much. I was talking with a customer about our project and telling them that we have to wait till next week because we are having problems still. Similar to others, I hate giving bad news. Its the part of my personality that hates the conflict of it, I’d much rather deliver on what I set out to do and do a 110% job. But not today.

For the past few months, I have been waiting to finish up our software platform. We have missed our deadline and significantly gone over budget. It has been a tough road as if I did it all, I would have been able to complete it (back in the day) in a much shorter time period. The worse part about it is that I outsourced the work after being convinced that this contractor was excellent in the field. The excellence hasn’t come out how I expected so far, and has just given me stress and anxiety…getting me to the point where I am now…a not so fun end to my Friday.

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Listening to Everyone, while Listening to No One

Just finished the first meeting with a new group of advisors with the Chicago Innovation Mentors group. I was accepted into this group as a startup company to work with 5 incredibly experienced startup advisors over a 6-month period as a Board of Advisors.

The first meeting was tonight. I prepared as much as I could for the meeting. I spoke to each advisor before the meeting and organized an agenda to cover topics I needed help with.  The meeting started without a hitch, it went very well according to the agenda. We introduced ourselves and got to know each other better than delve into the deep dive about the company. Understanding where we came from and where we are today. As you may have expected, we were bombarded with questions during this deep dive to help get the advisors up to speed on the company and what value we provide to the industry. It was very interesting to hear their thoughts on where we are today and their insights.

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10 Principles for Design in the Age of AI

  1. Good design solves an important human problem
  2. Design is context specific (it doesn’t follow history)
  3. Design that enhances human ability (not that replaces human ability)
  4. Good design is discreet (frictionless)
  5. Good design works for everyone every day
  6. Good design is a platform that grows with people’s needs
  7. Good design learns and predicts human behavior
  8. Good design brings about products and services that build long-term relationships
  9. Good design accelerates the adoption of new ideas
  10. Good design removes complexity from life.

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