Market Analysis

Insight & Inspiration From Our Portfolio Company Founders


One of the best things about being part of the DCA team is the exposure we get to so many talented and driven founders representing a wide variety of business verticals. It’s truly inspiring to be around that type of energy, and we often draw valuable insight from their unique stories, challenges, and milestone moments.

One common thread we found in many of the founders we’ve worked with is a strong altruistic desire to share their experience with other founders embarking on the epic journey of starting a business from scratch. For this blog, we want to share some of those pearls of wisdom. First, some introductions.

Katy Kappler is the Co-Founder & CEO of InScribe, an education-focused digital learning community platform and application that leverages the power of community and artificial intelligence to connect students, teachers and staff to the answers, resources, and people they need to succeed.

Ryan O’Neil is the Founder & CEO of Curate, a professional florist and catering / event  management software company that makes it easy to organize information needed for events and turn it into proposals, accurate recipes, and streamlined wholesale orders, saving time and increasing profitability.

Rebecca Clyde is the Co-Founder & CEO of, an AI driven conversational marketing platform enabling meaningful and intelligent communications between businesses and their customers.

We posed a series of questions to these successful founders, and their responses were both insightful and enlightening. Enjoy…

What is the one thing you did early on in the life of your company that had a huge impact on your success?

Katy-InScribe: When we started the company, my co-founders and I spent a lot of time talking about the culture we wanted to form and how we were going to protect that culture as we grew. This was before we had any other employees – but we knew from previous experience how a strong culture can impact all aspects of the organization – either positively or negatively. We wanted to attract and retain employees who would thrive in our company, and we wanted to build a place where we would love to work. And we have succeeded! We’ve grown an amazing team and have 100% employee retention to date. We spent a lot of time in the early days with validation. Before building the product, we conducted nearly 100 interviews to test our product idea and value proposition. Through each round of interviews, we iterated the idea to make improvements and home in more closely on the market need. Nearing our hundredth interview, the meeting ended with the comment, “How much would it cost? I want to be your first customer!”, We then knew we were ready to start building the product. We parlayed that meeting into a purchase order, which became our first check. Having that validation was critical to knowing we were on the right track and made all the difference when we eventually embarked on our fundraising journey.

If you could do it all over again, what would you do differently?

Katy-InScribe: When we first decided to raise money, we were new to the process and cast a really wide net across the investment community. That meant we spent a lot of time talking to investors who were not a good fit for our company and team. As a social impact organization, we should have focused on investors who are also in the impact space and who share our “double bottom line” approach. We found our way to this community eventually, but we could have gone faster if we’d spent more time up front to understand the investor landscape and how other impact companies have successfully navigated the fundraising process.

Ryan-Curate: I would hire strong leadership sooner. This would also require a bigger investment and can become tricky if you’re still learning how to hire leadership. It can be easy to mix up looking for someone who can be a great leader in your organization and someone who is asking for a proportionally large investment from the company. Just because you find the latter doesn’t mean you’ve found the former. The hard part is finding the right people that truly provide leadership, understand the importance of their role, have the skills/tools to lead, and justify the required investment. Building the right leadership team early is key.

What has been the most challenging time in the growth trajectory of your company and how did you navigate that?

Katy-InScribe: As our company grew and the team started to diversify, we had to make difficult decisions about how best to invest our dollars across the organization. We had to balance between support for current customers, the opportunity for ongoing product innovation, and the need to drive new business through sales and marketing. Ultimately, we looked at how each of these groups would impact customer growth and revenue potential over the next 2-3 years via renewals, increased price points and new customer adoption, and we used that measurement to guide resource allocation. We know that it’s a calculation that will change as we continue to grow, so we revisit it every quarter to understand if we still have the right balance.

Ryan-Curate: Probably the biggest challenge occurred after we landed our biggest deal ever, closing a transaction that was a six-figure deal.  After that experience, we decided to pursue more of these bigger deals and spent most of the next year doing so.  However, we eventually realized that a big deal like that was a one-off situation and not sustainable. It was our most discouraging time and I hadn’t yet brought in the leadership that I needed, so it was a challenging period to get through.

So how did we survive? We just refocused and worked through it. We had some difficult meetings and made some tough decisions.  It forced us to re-think a lot of things—we had to transition to a new approach, and many team members left the company. The change really came in 2020—we had to rebuild from the ground up in both the leadership team and at the key team member level. Overall, it was really important that we took a fresh look at what we were doing and then re-created the business in a sustainable way.

What has been the most rewarding part of starting and growing your own company?

Ryan-Curate: It’s rewarding in two dimensions.  A big part of it comes from the customers. We serve small business owners, and these are people whose livelihoods are built around our platform. We measure ourselves in NPS (net promoter score), and it’s important to us.  I’ve had experiences where I’ve been on a call with a small business owner, and they’ll be crying by the end saying how thankful they are for the work we’ve done—that’s really, really valuable to us.

You’re always going to get people who are frustrated about a certain customer experience, but you can’t let those occasional interactions lead to a bad day. What we have found most rewarding is, hands-down, the appreciation of our customers.

The other aspect that is really rewarding is learning about people—being able to build relationships with people, developing a good team, seeing your team come together, watching people step up to the plate at key moments, and giving people  opportunities—it’s a huge thing. We’ve dealt with so many ups and downs during the early stages, so it’s hard to appreciate the progress over time. But looking back at the last two years, I can see how far we have come—from an MVP (minimum viable product) with just a handful of customers to a highly sophisticated product with dozens of customers, who not only use our product but rave about the results they get. It’s worth taking a step back to marvel at the progress!

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