PJC interview: Openly

PJC Interview with Ty Harris, CEO & Co-Founder of Openly

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“We created Openly because there was an evident gap in the market for premium insurance made simple. Consumers should have more complete coverage at competitive prices. Our use of data, sophisticated pricing, cutting edge technology, and insurance expertise gives us the opportunity to bring something better to the market.”

- Ty Harris

About Openly: Openly is a technology enabled home insurance company. Ty describes the company as a modern take on a historically non-transparent & pretty inefficient industry & business. He explains that many people may fall prey to “gotcha” scenarios where they lack needed coverage during a claim, while expenses can be high. Additionally, it can also be hard to shop around and folks may not know the best way to do that. Insert, Openly. Openly allows for better coverage, drastically faster and all with a modern experience. Their centralized platform offers comprehensive coverage using advanced pricing models. Ty co-founded Openly with Matt Wielbut, who was a VP, Engineering at Goldman Sachs and brings the “tech” half of “insurtech” to the venture.

About Ty: Before founding Openly in 2017, Ty spent 12 years at Liberty Mutual, a top 5 global insurer, where he was most recently EVP and Chief Product Officer. In this role, Ty led an organization responsible for product, pricing, underwriting, and innovation across all personal lines of business. Prior to Liberty Mutual, Ty did research at the Brookings Institution and taught economics and statistics at MIT and Northeastern. A Duke and MIT alum, Ty is also a fully credentialed actuary (FCAS). Ty just recently moved to South Carolina with his wife and two kids, but lived for over 15 years in Boston’s Back Bay. He’s an enthusiastic runner, snowboarder, windsurfer, and dad!

What motivated him to start Openly: Ty’s motivation to starting Openly was rooted in his prior employment experience at Liberty Mutual, where he worked for 12 years. He said while he worked at a great company alongside many well intentioned people, there were times when he felt limited by being part of a large corporation. He had also been following other countries' trajectory in the insurance space and as he watched the space trend towards more transparency coupled with their success, especially in countries like the UK, he knew there was a good opportunity within the US to do the same.

On his experience with PJC: Ty says, “I met PJC very early in 2018, in the first quarter while we were at TechStars. The relationship has been really great. As an early investor they betted on us from the start without seeing a lot of results at first, as it took time to get to the market. They continued to do so in their latest round, and their trust in us has made a huge difference. For example, even in these tough times (COVID-19) while we were seeking an external raise, they reached out to talk through the options and do what they could to support us, and their industry experience really helped with our confidence in the raise.”

When asked what one or two words come to mind with PJC: Supportive across the board - supportive in not a fair-weather sense, consistently, & non-judgmentally supportive.


Top 5 takeaways from our interview

  1. Never hire anyone unless you are excited about it, emotionally excited; this goes for business partnerships, too: Ty explained that when you are trying to convince yourself to make a hire rather than listening to your gut instinct, or the excitement you have, it could lead to bad decisions later. In Ty’s words: “The underlying lesson being that you are always going to discover things that aren’t exactly what you may have envisioned from the onset, so if you have some bank of enthusiasm up front that you can draw from that is great, ….your instinct is usually right if you are not excited.”

  2. Be cautious of advice that says to optimize for valuation over raise. When I asked Ty what the worst piece of business advice he has received he explained that when he was beginning to raise money he was sometimes told to optimize the value at which they were raising money in a way that would bring him terrifyingly close to running out of money. He explains, “To a degree it’s a personal decision, but my view is: I’m taking enough risk by starting this crazy business, so I don’t need to take a ton of risk in the middle of getting funding to get a 10% higher or lower valuation. I tend to discount the advice that is looking to optimize valuation over raise, always take money, there are inevitably going to be problems you don’t see that will make you not regret taking a bit more money”

    *Openly began fundraising for their Series A round in March 2020, at the height of a global pandemic and with a lot of uncertainty on the economic landscape.  However, they were able to close on their 15 million fundraising round in June.  I asked Ty more on that decision and his experience with fundraising and received the following takeaways below.

  3. Investors right now are more comfortable with who they knew pre-pandemic. This isn’t too surprising, but Ty explains that having existing investors and connections from his previous round definitely helped in securing their Series A. Due to the limitations from COVID-19, those in-person relationships and meetings are less and coupled with an uncertain economic climate, this can create investors to be more cautious. Therefore, they are more willing to invest in an existing company, as it provides them with a better peace of mind. However, there are always exceptions, but having established those relationships up front was definitely a benefit.

  4. There are silver-linings to fundraising in the middle of a pandemic. Although, it's not ideal to fundraise in the middle of a pandemic, Ty found that scheduling and meetings became a lot more effective.  Founders who typically would fly out to pitch in person are now doing it via video and with that, a lot of time is saved.  Founders don’t have to worry about traveling and coordinating a busy schedule, and can actually schedule more investor meetings because of that.  Also, more investors and partners may join a meeting that typically wouldn’t due to time constraints, and office locations from your typical in-person meetings.

  5. [on fundraising] Build your network early, and be detailed with your CRM from the start.   The more times you pitch, the more opportunity you will get for future rounds.  Sometimes the timing is off and an investor may not be able to invest, or see it as a fit.  Things can change though and establishing those relationships upfront can go a long way for future rounds.  Ty also explains his strategy when fundraising, especially with this last round.  He knew he had to go into fundraising full-time and would rather go at it aggressively for a short time than spacing that effort out.  Additionally, he recommends building out a detailed CRM system from the start.  He said having been detailed with his CRM will allow for more time and effectiveness.

BONUS: Be sure to check out Episode #12 of Season One of The Uncovered Podcast where we talk to Ty about his journey to entrepreneurship and starting Openly in more detail. https://www.pjc.vc/podcast/season-1-episode-12

This interview was conducted on August 5th 2020. 

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