New Investment Series: Occasion

The Hyde Park Angels “New Investment Series” profiles our most recent investments by examining the investment process and the individual company’s future trajectory from two perspectives: the portfolio company’s CEO and the HPA leader who made the deal happen. This edition focuses on Occasion. 

Aksh, why did you start Occasion? What problem were you trying to solve?
Aksh: I was an avid tennis player in Chicago. Every time my friend and I went to get on a tennis court, we found ourselves waiting for over an hour. I thought to myself there has to be a better way. We became members of a private tennis club thinking that would solve the problem of getting on the court. Instead, we found ourselves playing “ping pong” on the phone with the front-desk person taking reservations. It was then I said I’m just going to build a tennis court time reservation software and sell it to tennis clubs. I launched the product in it’s very basic form and then realized there was a much bigger market for a product like a simple booking software.

Every service-based business owner has three problems: giving customers an option to book their offerings quickly, growing relationships with their customers, and growing revenues. We solve all three problems in the most effective way possible.

So then, did you always plan on raising venture capital for Occasion? What led you to pursue fundraising?

Aksh: No. I come from a family for at least three generation of entrepreneurs, all of whom built businesses by bootstrapping. Raising outside capital was a very foreign concept to me. It was not until I realized the enormous size of the opportunity that I knew I had to raise outside capital to grow fast.

Building relationships led to going to as many office hours as humanly possible hosted at 1871. Click To Tweet

What was the single biggest step you took to prepare for fundraising?
Aksh: It was starting to build relationships by going to as many office hours as humanly possible hosted at 1871. I knew no one but I thought going to office hours would be the quickest way to get connected to the right people. It took some time but it worked.

Gib Olander, HPA Member & Deal Lead

Gib, switching it over to you, what first sparked your interest in Occasion?

Gib: There are market trends of mobile commerce and the on-demand economy that are enabling disruption. I liked that Occasion was well-positioned to help an interesting segment of businesses take advantage of these trends.  After I met the Occasion team I was impressed by their grit, financial discipline, and passion for the problem they are solving.

Following up on that, how did you leverage your background and expertise to evaluate Occasion?
Gib: In the past I’ve developed and sold products which have been purchased by more than one million SMB’s.  In evaluating their lead gen efforts I have been impressed with the Occasion go-to-market strategy.  As the Vice President of Product for a software development company it was easy to see that Occasion has developed a sophisticated SaaS platform that meets their client’s needs.

What makes the current group experience bookings space an attractive market? What are the advantages and disadvantages of playing in this market?

Aksh: Millennials are the future of business. Millennials crave experiences, more over they are hungry for group experience. Things to do with their friends, family and team. And, they demand immediate gratification. This is going to create a whole new generation of businesses built around satisfying this bottomless demand. And, those businesses will need a set of tools to run their operations. Occasion is positioned to take advantage of that market as it develops.

I don’t see this so much as a disadvantage but a risk. Our solution is an enterprise solution and it just happens to be for small enterprises. Business workflows needed for a running a small enterprise are not different than those required to run a large company. At Occasion, we remain vigilant of this fact.
How do you plan to work together in the future?
: I am very excited to have Gib’s mentorship available to me and the rest of the team. Gib has built businesses in the space and has a deep understanding of how to scale a company like ours. His experience is going to help us not just grow but also avoid making mistakes while we execute.

Gib: It’s a privilege to be a Board Observer for Occasion, where I can use my experience and network to help the team with product scaling ideas or issues as well as help with partner and sales introductions.

What should entrepreneurs seeking capital do to get a leg up on the competition?
Aksh: I can only share one thing which I am a beneficiary of – which is building key relationships early on. I think of relationships as nodes in a network. The more “nodes” I am connected to, the stronger my network. It leads to two things – these relationships open up new opportunities and help validate me in the network.

Relationships are nodes in a network. The more nodes I am connected to, the stronger my network. Click To Tweet

Gib: Prove product market fit by getting clients to pay for your product and be able to demonstrate how you will be able to scale your approach to client acquisition or other monetization strategies. You also need to identify unique market trends or conditions that will allow for your disruption to take hold and grow.