The road to success is long and arduous, there is little doubt that only the strongest (and luckiest) survive. Along the way you will experience amplified highs and lows, with the lows obviously more difficult to deal with.
Someone once asked me “what was the lowest point during the history of your company?” I hadn’t really thought about it prior to this question, but my memory zeroed in on a specific moment almost immediately.
It’s not just one thing, it’s the sum total of many things happening in short succession that cause the most intense highs and lows we experience in life.
The early days of any bootstrapped startup could be referred to as desperation mode when it comes to customer development. Any logo at any cost is the name of the game, even if it means building an entire feature set just to please a single key brand. It’s easy to get taken advantage of because most B2B buyers are aware of this reality.
Other manifestations of desperation mode include willingness to travel just about anywhere at just about any time, manually fudging work you have sold as “automation”, offering discounts or other incentives, and promising features or capabilities by some future date.
It’s important to note that at this time in the company’s history there was almost no revenue - barely enough to pay the AWS bill. There was no payroll, no office. Personal capital was burning by the hour. This factor adds quite a bit of weight to everything that happens, both good and bad.
The perfect storm
The story of the lowest point is a convergence of several disconnected situations that randomly came together in a single moment. I suppose this is typical of any apex scenario, whether good or bad. It’s not just one thing, it’s the sum total of many things happening in short succession that cause the most intense highs and lows we experience in life.
The day began like any other - and had the makings of a historically good day for the company. Three major items were on the agenda, two were customer related and one was more strategic. This last item was scheduled for the end of the day and would prove to be the cherry on top of this shit sundae.
Before we jump to the end, let’s back up to those customer wins for a moment. The first was something that had been in the works for about six weeks. A prospect had asked for additional functionality during the free trial process. Their request happened to align well with the product and was already on the future roadmap, so it made sense in those early days to move it up the priority list to get the business. In addition to the normal routine of running the business, I found the time during those six weeks to code up the requested feature to lock down another sale. And now it was time to close it.
The second customer development task for the day was an on-site visit to a local well-known public company. I had worked with someone who had recently taken a C-level job there, and this individual got me an introduction to the buyer. On the down-low, my ex co-worker had also assured me that they’d be an early adopter since it was obvious they needed the product. He just wanted me to pitch the person down the chain who would ultimately make the buying decision with his recommendation and approval. In the first year of a bootstrapped startup, these relationships are crucial in landing those first tough customers.
An actual storm
The geography of the Seattle area sometimes leads to strange weather patterns. I needed to get to the west side of Lake Washington to find parking and take my first call from a coffee shop. It was a fairly nice day in early October as I walked out of my house.
By the time I got across the bridge, the rain had started. And it wasn’t that typical, misty Seattle rain. It was a torrential downpour. The sunshine and rainbows of the east side had fooled me into under-dressing, and I didn’t have an umbrella.
After struggling to find parking I ended up 6 blocks from the building; my clothes were soaked through by the time I got to the lobby.
Even though I looked like a drowned rat I was still excited about the meeting and ready to sell. Alas, it wasn’t to be.
In less than 10 minutes the person responsible for email marketing confided in me that they were already under investigation for some random CAN SPAM shenanigans and could not risk bringing in another top of the funnel email vendor.
This had been one of the most important slam dunk customers I had identified due to my relationship within the organization. It is always particularly difficult to lose a deal at this stage - we tend to look at relationship-based sales as already in the bag. One lesson I learned early and often is a deal is never in the bag.
We shouldn’t have to pay!
Okay, back to the grind. Rather than drive back to the east side I took the next meeting from a Starbucks. I hadn’t yet learned my lesson, so I dialed up ready to talk in my best slam dunk voice.
This customer had first seen a demo about 2 months prior to this scheduled meeting. The buyer had shown a ton of interest and big time intent to buy. There was only one problem: a planned feature was critical to her use case and she wanted it finished before purchasing.
The feature was on the roadmap, it was just scheduled a few months out. Once again desperation mode called and I needed to answer. Over the course of the past few weeks I found a way to work on the desired feature. Translation: I worked nights, weekends, and pretty much any other time I could spare.
I got on the phone, excited to demo the new feature and get the deal closed. And man did I need it after the morning I had. I went through the demo, the customer was happy with the feature.
Then, she said something totally unexpected:
Since we helped identify a feature needed in your product our first year should be free.
I didn’t know how to respond, but she continued… “you’ll be able to get more business and close more deals because we asked for this feature. Thus our first year of using your product should be at no cost.”
It wasn’t easy, but I didn’t lose my shit. I calmly explained to her that we already had that feature on our roadmap and had accelerated it past other things to earn her business. We would not have done it without the incentive of closing the deal with her company upon completion. To make matters worse, I had already quoted her a massively discounted price for our lowest SKU, $100/month at the time.
Alas, it was not to be. She thanked me for doing the work and let me know they’d reach out if they were interested in continuing with a paid plan in the future.
I never heard from her again.
The coup de grace
Despite these losses I was still feeling okay about the day because the biggest event was planned for last. Someone I had known and worked with in the past was going to join me as a co-founder. We had been working on the terms for a few weeks and this was the day we’d be making it official. The meeting was set for around 3PM in the afternoon at the company lawyer’s office.
About 20 minutes after I hung up with Ms. “I don’t wanna pay” I got a call from my future co-founder.
It wasn’t good news. He had decided that the risk of joining a bootstrapped startup was too high. He had just recently been given a big promotion at his current job and his third baby was on the way. It just wasn’t a good time.
I understood, of course. Given the events earlier in the day I was already feeling the risk and pain that goes along with building something in those early days. I was not going to try to convince him otherwise.
The lowest moment
It had arrived - the lowest moment I can recall in the history of the company. To recap, in the course of five hours:
- A slam dunk enterprise customer that would have added legitimacy to the product and a doubling of current revenue had given a firm no
- The customer who had gotten a feature moved up on the roadmap - distracting me from other efforts (more sales perhaps?) had also said no
- The co-founder who I’d spent weeks with working out details and planning the future of the company with had to say no
I remember sitting in my car that afternoon in a parking lot for about 45 minutes. I couldn’t go home yet, I needed to get my game face on before walking through the door and hearing the inevitable question “how was your day.” The literal tears in my eyes wouldn’t play well.
In these moments we must somehow find the strength to keep positive. Otherwise we risk self-despair and the added stress of our loved ones seeing on our face how dire the situation is. Or at least, how dire the situation feels at the time.
It’s also in these moments we find out who we are and why the rewards are so great for resiliency and the ability to take a punch. Not just take a punch, but wake up the next day with even more energy and confidence that you will succeed than ever before.
If all that sounds like fun, you might be ready to bootstrap your company.