Chasing Dollars: Three Failed Attempts To Get Outside Capital

Chasing Dollars: Three Failed Attempts To Get Outside Capital

This first appeared on the INFLECTION Blog

On three occasions I chased outside funding when I should have just buckled down and focused on getting consistent predictable revenue. Here are 3 of those occasions:


After getting a bunch of investor rejections (as mentioned in the prior blog) I decided to look for alternative forms of funding.

Classically, funding comes from a loan, and there were many new upstart loan providers who seemed forward-thinking. Many of them had rough payback cadences and high interest rates, but I sifted through them and found one that seemed like a fit. Their main selling point was that I would have cash wired to me “within days”.

And within days… nothing happened. For the next few weeks (i.e. not “days”) I poured approximately 17,0000,000 seconds into emails and calls requesting and re-requesting documents. I was repeatedly told over the phone that things looked good, and I could expect a wire soon, just going through the formalities with the underwriters.

The underwriters were spooked by a few things:

  • I called myself an engineer but I ran a t-shirt company

  • I posted on Facebook that we were shutting down our subscription program to focus on the bulk b2b (business to business) side.

I tried to explain, but once you get into one of these scenarios, their mind is made up and no amount of logic will explain away the fear.

This deal was done, and I had to move on.


I walked into the office in South America and saw an entrepreneur at the photocopier, staring blankly. I already knew what was happening. “Expenses?” I asked. “Yeah.” he said with a sigh.

This was the standard part of the process when searching for “free money” in south america. There are equity-free grant programs that promise you the world. But, my friends, nothing in life is free.

I had gone through one round of this type of program before. Despite the pressure, it can be a really good time, and you get to meet other like-minded people. Entrepreneurs who flock to equity-free grant programs like this one, regardless of their ideas’ potential or anything else, are kindred spirits. It was only by attending these programs like this that I found critical people (like Devin Baptiste, an incredible human being) who helped me find consistency, cadence, and measurable ways to improve the business.

There were downsides and struggles, but I jumped through the financial hoops and presented on demo day:

The program ended up adding a second program, this time for $100k. They accepted my proposal, and with . fond memories I went back to South America for the second time. It was not the same experience.

From the start, I struggled to get a visa code from the program to even get the work authorization to come back down. The money was delayed by 4 months to start and was setup in batches:

  • An entrepreneur receives the first half of the funding.

  • Entrepreneur shows the finance team how the money was spent.

  • Entrepreneur then gets the second half.

The caveat is that if there was an expense on the US account (e.g. in the 4 months when I was waiting on the first set of funds), the entrepreneur would have to show a transfer from the South American account to the US account, even if that transfer happened after the payment.

So what did most entrepreneurs do? They transferred money down to South America and then back to the US. This process takes a month or more so more ambitious founders did the logical but shady feeling thing: travel with a duffel bag filled with $9,999 (the legal limit) in order to deposit in their South American accounts. That took about 24 hours instead of 30 days.

My struggle was with the approvals. I submitted expenses for an entire year back and forth and had them rejected for all kinds of unforeseen reasons (e.g. wrong currency listed, no phone number on an invoice, staff being away or unresponsive etc).

I’d spent some of my fulfillment money on main expenses while I waited for this cash to come and it created a cash crunch that I wasn’t able to recover from. It made customers (understandably) mad but I had kept hope that we would work it out. I could not even imagine a startup incubator not paying someone $50K that was owed to them.

After a year of trying (thats not a typo or exaggeration. A full year.), my expenses were finally approved. Here’s the rub: my contract said I needed to show my second half expenses by 2 weeks before it was approved.

So I flew down to South America from the US (over 36 hours of travel) for a one hour meeting that ended up lasting 15 minutes.

I walked into the office that fateful day that I saw the entrepreneur at the photocopier. After waiting for the executive to show up, he finally appeared and we went into the dingy conference room as I started explaining:

“So I wanted to see what we could do about this as I was told wrong amounts to transfer…”

“I don’t care.”

“Excuse me?”

“I don’t care Frank. I know I said the wrong thing but it’s free money. Tell whoever you want, but I don’t care.”

My friends know me as a chill guy, but this sent a rage in my body I hadn’t felt in a while.

Logic took over and I just ended the meeting and headed on the long flight back to the US.

I haven’t been back there since.


I sat at the edge of the pool in San Juan, Puerto Rico, talking with my friend Lester about his company. He was throwing a pool party and we sat there talking about his plans for growing EBITDA and what methods he was thinking about to grow the business. Next to him was my friend Jon from Chicago, who had been teaching me salsa and is the funniest person alive.

I had found my tribe.

After the frustrating experience in South America, I was given a lifeline by being accepted into Parallel18, a startup program in Puerto Rico. Everything about it was beautiful, from the weather, to the program structure, to the financial process, the mentors. I worked in my “corillo” (peer group in Puerto Rican parlance) to continually build up my business.

I found a super intern Natalia who would go on, with her twin sister Samara, to build a company afterwards called Banquetealo. If you’re ever in Puerto Rico, you should use them for catering (#notsponsored).

I presented on demo day and felt the tides were turning as we transitioned from Startup Threads (a brand that neither catered to startups or only did threads) to INK’A (which stood for engaging your leads and customers with high quality branded goods).

The pitch was clearer and I felt like people were starting to understand my vision better:

My mom came and she finally turned the corner with understanding this entrepreneurial urge we have. There were so many times where I wasn’t sure if what I was doing was going to work and she also was worried, but felt reassured by the demo day.

After demo day, I made the decision not to come home to New York but to permanently move to Puerto Rico, even after the program had ended. After all, I had found my tribe.

Some investors were impressed with the pitch and I had rounded up a group of funds and angels that would put the first $250K into the business. This is “not a lot of money” for many in Silicon Valley, but to me, I was able to turn $60K in grants into $2mm in revenue, so this money would be transformative to the business.

We had gotten to the point of checking out the new co-working space that the lead investor wanted me to work out of in old San Juan with a view that was to die for. We were working out the paperwork for them with my lawyer.

On that lovely Saturday evening talking to Lester and Jon by the pool, my friend Jose Falcon showed me his phone: another hurricane was coming to the island. We had recovered quickly from Hurricane Harvey so I didn’t think much of this Hurricane Maria that he was worried about.

Care-free a few hours before the Hurricane Maria alert went out

I woke up on Monday morning (Sunday was rough) and my normally perma-smile roommate Mike walked into the living room with a scowl:

“So what’s your plan for Maria?” he asked.

“I got some extra bread and canned tuna. I didn’t find enough flash lights though, do we have any left at your dad’s place?” I said.

“Dude. You need to get the fuck out of here.”

He was right. I didn’t have much money at the time, but I had a flight planned for the next week to New York to shoot this commercial for Land Rover:

I called up JetBlue and they said there were 3 seats left on a flight the next day on Tuesday and they would change my flight for free. I took it.

I was texting with my lawyer that Tuesday, and he mentioned his power was probably going to be cut off so we couldn’t finish the paperwork until later. No worries, we’ll get to it next week, I thought.

The next day on Wednesday, the worst hurricane in 100 years hit the island. More than just being a temporary set back, it changed the lives of everyone on that island, and mine as well. Apart from the financial stressors and the threats to my business, Hurricane Maria felt like a personal attack. I had found my tribe, and she had brutally attacked them.

The investors I spoke to decided to leave the island and no longer had the same conviction about my company. Disaster puts a lot of things in new relief. Funds halted operations and people who had been my champions in Puerto Rico left their firms to save themselves with jobs in the US. The $250K that I had circled was wiped out in the tempest.

My struggles pale in comparison to what many hard working Puerto Ricans had to (and continue to) face with the aftermath of the hurricane and the US’s sub par response. But it doesn’t make it hurt any less.


It would be simple to chalk up all of these experiences to bad timing, bad luck, or just once in a century flukes. But the circumstances I was in and the focus I had were my decision.

If I had chosen to focus on growing the revenue we had, cutting unnecessary costs, and building a better model like Adam Schwartz suggested, I would have had less of a need for outside capital.

These experiences led me to today, so I have no regrets. I just had to learn these lessons the hard way.