Demo Day, then back to the negotiations
I look happy in the photograph with Giuseppe outside Demo Day. I was happy. I was also exhausted: I had spent the night dealing with an existing investor who opposed the flip, the reorganisation of our company under a US parent.
Our Demo Day was 19 March 2019. After months of preparation, we had a chance to put Askdata in front of investors. I would have preferred to arrive after a good night’s sleep. Instead, a difficult negotiation followed me right up to the event.
That is one of the things a photograph cannot tell you. You can see the matching shirts, the badges, the coffee and the smiles. The corporate restructuring is harder to fit in the frame.
The flip mattered because we were building a company that could raise capital and operate across borders. It involved people who already had a stake in the business, each with their own concerns. Explaining the future you want to build does not make those interests align automatically. The night before Demo Day, that was the work in front of me.
I felt an enormous amount of pressure. There was the opportunity itself, and there was the fear of arriving too tired to do it justice. We had come a long way from the little Airbnb in Redwood City and the interview in November. Now we had to explain Askdata clearly enough that people would want to continue the conversation.
The fundraising brought backing from Silicon Valley, other North American and Italian funds, as well as individual angels. I am keeping the amounts and fund names private. What I want to remember here is how it felt to move from presenting the company to getting people to commit to it.
An investor’s interest gave us another set of things to do. More questions, another conversation, terms to discuss, documents to get through. We worked around the clock to keep the process moving. The excitement was real, and so was the administrative weight of it.
FOMO was part of the atmosphere. Once investors knew that other people were interested, the pace of a conversation could change. You could feel how much attention was influenced by what everyone else might be seeing. Being on the receiving end was exciting. It also made it harder to judge how much of the enthusiasm would survive the next step.
I cared about turning that attention into decisions. There was a large practical difference between someone liking the company and someone completing an investment. We had to keep answering questions while negotiating carefully, at a time when every delay felt expensive and every positive reply made it tempting to assume the hard part was over.
Some of the people who backed us were especially exciting to me. Nick Caldwell, then Chief Product Officer at Looker, joined as a business angel. Looker was one of the most exciting companies in analytics. For us, working on how people interact with business data, having Nick invest meant a lot.
He knew that world from the inside. I was proud that someone with that experience wanted to back what we were building. The conversation could begin with the product and the problem, with much less distance to cover before reaching the interesting questions.
There was a good deal of negotiating through that period. I do not remember it as a succession of smooth meetings leading to a neat conclusion. I remember the workload, the uncertainty, and the need to stay responsive while still thinking clearly about what we were agreeing to. A successful raise contains many small decisions that do not appear in its announcement.
I also remember the pleasure of it. People were committing their own money, or their fund’s money, to a company Giuseppe and I had built with the team. That is an extraordinary vote of confidence to receive. I wanted to enjoy it, even while another email or document was waiting.
The days around Demo Day put those feelings very close together: ambition, fatigue, pride, irritation, relief. The same person could be delighted to have an investor meeting and desperately wish for an uninterrupted night of sleep.
I like that photograph of the two of us. We are standing outside, in our Askdata shirts, and I have a coffee in my hand. It keeps the happiness of that day. I remember the rest as well.