Tag Archives: Chris Cheatham

The Next Wave of Insurtech

At the recent International Insurance Society annual meeting, panelists laid out some intriguing thoughts on insurtech, saying that the first wave is ending and describing the outlines of the second wave that has already begun to form.

The key takeaways: 1) The industry is focusing too much on what panelists called “the shiny objects,” like artificial intelligence, and not enough on the issues that really matter to customers and to corporate bottom lines; and 2) incumbents will bear much of the responsibility for whatever success the second wave has, depending on how well they retool their mindsets and their processes to absorb the steady stream of innovations that smaller players will provide.

The best image: the mullet. That’s how Jamie Yoder, president of Snapsheet, characterized innovation in insurance to date. “There has been so much attention paid to the front end [basically, sales],” he said, “but there’s a huge opportunity to clean up the back.”

In addition to Yoder, whose young company digitizes and automates the claims process in personal lines, the panel consisted of: 1) Chris Cheatham, who founded a startup, RiskGenius, that uses AI to facilitate review of policies and that was recently acquired by a bigger startup, Bold Penguin; and 2) Jeff Berezny, SVP and general manager of enterprise products at Trov, which provides a digital technology platform for incumbents. The panel was moderated by James Maudslay, global head of insurance at Equinix, which operates a huge network of data centers. (You can watch the entire session here.)

Yoder argued forcefully that much of the focus for innovation is on the wrong issues. He said that the sexy part of what Snapsheet does is the computer vision that can analyze photos of damage in a car crash and use artificial intelligence to provide an estimate of the cost of repairs. But he said computer vision saves only maybe 15 minutes on estimating — in a claims process that can languish for days. He said he can get from a first notice of loss to a settlement in 30 minutes, but the computer vision only works in 1% of the cases. Why not, Yoder asked, focus on the big delays that happen as the insurers for those involved in a crash gather and exchange data, sort out responsibility and get money to clients so they can get their cars repaired?

He said the secret to innovation isn’t to have AI do the estimate. “Al will do,” Yoder said. [Lest his joke doesn’t come across in print: He’s saying that Al, as in someone perhaps named Albert, could do the work that everyone seems to want to assign to artificial intelligence and still allow for considerable innovation.]

“The real issue is all the handoffs,” Yoder said. The solution is to “have the claim be the captain of the process. It’s determining, what can I do myself? It’s assigning tasks to vendors, updating the customer, getting an issue to a person when it needs a person.” At the moment, he said, claims processes are managed “based on massive diaries and to-do lists, which don’t really foster efficient throughput of work. And this is in a piece of the business that is 70% of the cost.”

He said it’s also crucial to focus on all parts of the process, because so many can yield improvement. “We’d do all this work with carriers to speed their claims, then find they were still cutting paper checks,” Yoder said. “It’s like you decide to drink a diet Coke but then order a Big Mac to go with it.”

Berezny agreed that the beginning of the claims process “is just phone tag. Call me back, call me back, call me back….” So, having AI that manages the process, to reduce the administrative load on people, and that speeds the handoffs would matter much more than AI that prepares an estimate.

He said the second wave of insurtech that is taking shape now will be more about “selling picks and shovels” and not about the “gold rush” that is being capped off now with the huge valuations that Lemonade and Root achieved following their initial public offerings.

But he said the incumbents have a lot of work to do to prepare. While being cloud-based and digital are table stakes for being able to innovate these days, Berezny said, “Insurance just isn’t there yet.”

Yoder said incumbents need to develop modular processes, based on application programming interfaces (APIs), so companies can have “plug-and-play innovation.” Are information systems designed so “you can just plug your innovation in, or are you stuck with a new wave of IT integration projects every time” you see an insurtech whose software could improve your business? “Innovation isn’t about a point in time. This is a journey.”

He said the need to be able integrate innovation quickly is all the more important because so much is becoming available. Yoder, who until two years ago ran the insurance practice at PwC, said clients used to need to invent a host of capabilities to be able to pursue a digital strategy. “Now,” he said, “you can just pull together a list of insurtechs with those capabilities, and there you go. You should get there a lot faster and for a lot less money.”

Berezny said he sees the new wave of insurtechs leading to “not just direct but embedded” insurance. As a result, he said Trov is working with mortgage groups to embed home insurance in their sales processes, with new digital banks to offer insurance as part of their portfolios and with affinity groups to include insurance in their dealings with members.

“Insurance needs to meet people where they are,” Berezny said. “You can’t just assume they’ll come to your great, shiny website.”

Yoder agreed that embedded insurance has great promise. “People sometimes look for innovations that are way beyond what anyone ever thought of,” he said, “but sometimes the opportunities for innovation are staring you in the face.”

Cheatham said that, with “the first wave of insurtech coming to an end,” he hears a lot about how AI will supposedly eliminate human jobs. But he said the second wave will be about “augmenting humans, not replacing them.” In commercial insurance, where RiskGenius and Bold Penguin focus, “There are too many nuances for us to think that we’re going to get rid of humans in any part of the process.”

He said that innovation in commercial lines moves more slowly than in personal lines, where Trov and Snapsheet live. But he said, “We’ve shrunk processes from weeks down to days, and we can go so much further. I see a big acceleration going forward.

“We’ll catch up to you other guys soon enough.”

Stay safe.


P.S. Here are the six articles I’d like to highlight from the past week:

2021: The Great Reset in Insurance

A shift toward greater corporate and social responsibility and empathy in general is underway, and 2021 will bring a great global reset.

Innovating Our Way Out of a Crisis

Any requirement, process, delay or regulatory cost that does not serve insurer solvency or consumer protection should be on the table for retirement.

Ecosystem-Based Business Models

More insurers now see ecosystems as an effective, flexible and capital-efficient way to grow the business and promote customer-centricity.

3 Must-Haves for a Self-Service Portal

A hybrid approach to customer service appears to be the most appropriate strategy, smartly balancing self-service and human support.

Time to Move Climate Risk Center-Stage

Insurers face a steep learning curve in embedding climate risk into their enterprise risk management programs, but the climb will be worth it.

Free Insurance Data You’ll Need

I’ve been building and reviewing business plans for years and come across great free resources to help me along the way. Here they are.

A Glimpse of the Future of Insurtech

Today’s announcement that Bold Penguin is acquiring RiskGenius marks a milestone in the maturation of the insurtech movement. I’ve known Chris Cheatham, the co-founder and CEO of RiskGenius, for years and have closely followed the developments of what I have often described as my favorite insurtech. So, under embargo, I chatted with Chris to ask him to summarize how he surfed the first wave of insurtech so successfully and where he sees the movement going from here.

The deal feels to me like maturity because it exemplifies how insurtech has moved past some early ideas (e.g., that a Big Tech company like Amazon or Google would invade insurance and lay waste) and some early models (such as peer-to-peer provision of insurance coverage) that have yet to pan out. Instead, the Bold Penguin acquisition of RiskGenius exemplifies what I suspect will be the dominant model for some time: one where a company acquires a smaller firm for a particular skill or technology and incorporates it into the acquirer’s products and services.

I realize that Bold Penguin is itself only four years old — I wouldn’t be surprised to see it eventually acquired by an even bigger company — but it already had some heft, having raised over $50 million, and has added RiskGenius’ 24 employees and $13 million of capital.

As Chris explains the fit, “Bold Penguin focused on delivering commercial insurance faster, getting the insurance bound and issued faster. We help people analyze insurance coverage faster.”

Bold Penguin provides an online exchange where brokers can request quotes for clients, which tend to be small and medium-sized businesses seeking nonstandard coverage. The exchange automatically matches those requests with carriers that might be interested in providing coverage, solicits quotes and feeds offers back to the broker and its clients. The process still requires manual underwriting, so it’s not like you hit “Done” and instantly get your car insurance quote, but going from start to finish generally takes days, not weeks, as can happen with completely traditional processes.

RiskGenius fits in because it uses artificial intelligence to analyze policies, down to the level of individual clauses. Want to know how cyber coverage compares across policies? RiskGenius can find the relevant language for you, arranged for easy comparison. Want to see at renewal time how an insurer’s policy has changed? RiskGenius can help you sort that out, too.

While Chris built a successful stand-alone business (out of that well-known insurtech hot spot Kansas City, Mo.), it seems to me that RiskGenius nests better inside Bold Penguin. Brokers using the Bold Penguin platform will not only get quotes from insurers but will now have a tool they can use to sort through the details of policies and to help customers understand those policies.

Bold Penguin’s acquisition of a feature/technology for its platform very much fits the model in Silicon Valley, where some startups don’t even try to build a full business. Why bother to build a marketing or legal operation when the acquirer only cares about the technology and would surely shed all the operations people anyway? So, I expect to see more narrow-bore deals like the takeover of RiskGenius.

“If you think about commercial insurance,” Chris said, “there are just so many complexities. An innovator should just focus on one thing to fix.”

He said he thinks the first wave of insurtech is ending, while wave two is just getting going. (I’ve seen people say that the first wave has passed startup phase and is into “scale-up” phase, as the best prospects have now identified themselves and are attracting big chunks of capital.)

He is seeing more focus on back-office technologies that can create much-needed efficiencies and less on the sorts of distribution opportunities that showed up so frequently in the first wave of insurtechs, but he generally sees a host of opportunities because of the pandemic.

“COVID-19 has just changed the way commercial insurance will be purchased,” he said. “The number of people buying online has surged in the past six months, and that isn’t going to change. That cup of coffee to get to know someone or to review policy details just isn’t going to happen.”

Chris picked his own niche in classic fashion: He got annoyed at a problem and started a company to fix it, then pivoted when a customer pulled him into a new area that resonated much more broadly. Oh, and he got a little lucky, too.

After law school and a stint at a large firm, Chris became a solo practitioner and worked with clients on claims in the surety and insurance realm. Frustrated with all the paper he had to deal with, he started a company to digitize claims documents.

A customer had a better idea. An underwriter from a big insurer called him in 2014 and asked if she could use his technology with policy documents. Chris and his co-founder, Dan Burchett, agreed and began applying AI to the documents to do even more to help brokers with policy reviews.

“Policy reviews can take days to weeks if they’re really complex,” Chris said. “Even if a review just takes an hour, if you have lots of small accounts that’s still a huge amount of time.”

Chris’ approach to attacking that problem made so much intuitive sense that he quickly developed a following among those of us following the insurtech world. He was still scrounging for customers, but then the good fortune kicked in. Rick Huckstep wrote a piece about RiskGenius in the Daily Fintech newsletter in January 2016 and called the company “the Google of insurance.”

How can you ask for anything better than being called the Google of insurance?

“I was in Iowa doing the conference circuit,” Chris said. After getting off-stage, “I opened my phone, and it was flooded with messages. I was standing next to my sales guy, and I thought, ‘My gosh, we found a problem that is massive and worth solving.’

“We wound up with hundreds of leads. We never had leads before. I thought, I like this better.”

The rest, as they say, is history — except that I suspect that the RiskGenius deal is also the future. While a few companies like Lemonade will try for massive scale on their own, I think there will be a lot more deals that will pull a capability from an insurtech into a company that can deploy it as part of a broader offering that will have much more impact.

Stay safe.


P.S. Here are the six articles I’d like to highlight from the past week:

Why Haven’t More Startups Failed?

Insurers appear to be focused on tactical initiatives that can produce more immediate results in the pandemic, and insurtechs have the tools.

Optimizing Insurance’s Role in the Pandemic

Policymakers must thoughtfully position insurance industry capabilities where they can have the greatest impact. Here is a proposal.

COVID, and How to Pivot to Innovation

The pandemic has almost shut down entire industries, forcing companies to adapt — and doing incredible things for a pivot to innovation.

6 Cybersecurity Threats for Insurers

The insurance sector faces a bigger threat than most industries because insurers deal with extremely sensitive data.

Secret to Leadership in Insurtech Innovation

You need more than a product. You need to surround the product with proper execution, the right people and sustainable partnerships.

Managing Customer Opt-Ins in New Normal

Insurers need a single source of truth on opt-ins and opt-outs across the enterprise to solidify the relationship with the customer.

7 Things I Learned at Bold Penguin

This is my first week at Bold Penguin… marking the true beginning of my insurtech life.

I’ve followed insurtech for more than three years, writing and speaking on the movement, but my vantage point has always been one of the intrigued outside observer.

And while one week does not make you a qualified insurance technology startup guru, here are my first seven insights after diving headfirst into my new role as chief marketing officer at Bold Penguin.

1) Small Business Insurance Is the Holy Grail

McKinsey & Company has been referring to the SMB market as one of the “few bright spots” in the property/casualty insurance sector for years now.


Because no one owns the small business insurance space. The marketplace is fragmented, and generally speaking the commonly accepted customer experience is poor at best. Yet, done right, small business insurance is a growing and profitable market segment.

This is by no means breaking news.

That doesn’t diminish the fact that no one has small business insurance figured out, (except maybe…), making the SMB market the holy grail of meaningful organic growth for the foreseeable future.

2) There Is No Road Map

In case you’ve never worked for a startup before, there is no road map for success.

Insurtech startups are creating solutions that haven’t existed before. Look at the work that Chris Cheatham is doing in policy automation at RiskGenius or Mike Albert and Allan Egbert are doing in open APIs at AskKodiak.

Quite literally, they’re making things up as they go along.

…because they have to. The work lives in uncharted waters.

My point is, just as insurtech startups must mature into the greater insurance ecosystem that has existed for more than 400 years, the more traditionally oriented organizations (and individuals) must accept the slightly more haphazard nature of startup companies.

Insurance carriers with open-mindedness to the realities of trailblazing startups will position themselves out front as the partners of choice for insurtechs mapping solutions for our industry’s most challenging obstacles.

See also: An Insurtech Reality Check  

3) There Is a Race to Remove Friction

Research from a McKinsey & Company survey shows a 73% increase in customer satisfaction when customers reported they were pleased with the entire customer journey, not just specific touch points.

Winners and losers of the digital insurance revolution will be determined in the race to remove the most friction from the customer experience.

This doesn’t mean removing human agents or blowing up the traditional insurance carrier model. Rather, we must think of insurance as a service and create flow throughout the customer journey.

I joined Bold Penguin because it’s my belief that their solution will be the foundation upon which many winning agents, brokers and carriers build their unique customer journey.

Whether you partner with Bold Penguin or not, make no mistake, the race to remove friction is real and it’s happening right now.

If your organization is not having serious conversations about the customer journey, you’re already losing.

4) It’s Time to Ask “What if?”

It’s time for everyone to start asking “What if?” when it comes to the future of insurance.

  • What if APIs are the future?
  • What if customer experience is all that matters?
  • What if we can’t build it ourselves?
  • What if half our agency plant retires in the next five years?
  • What if our carrier partners demand digitization?

Whether you believe these scenarios will come true or not isn’t the point. The insurance marketplace is changing rapidly and being prepared for all the “What if?” scenarios possible is the only way to survive…

…because no knows what’s actually going to happen.

5) Disruption Is Dead

From now on, every time you hear the words “disruption” or “disruptor” come out of a startup’s mouth, your insurtech B.S. alarm should leap to life, the blaring sirens and seizure-inducing flashing lights overwhelming your senses while an impenetrable B.S. Protection Barrier envelops your entire body like some scifi force field.

Seriously though, disruption is not the answer.

Instead, insurtechs should focus on collaboration, facilitation and integration with traditional partners, building on the previous foundation as much as possible and alongside where it does not.

6) Culture, Culture, Culture

I’ve seen first-hand the impact a toxic culture can have on organizational success.

We live in a tumultuous time for workplace culture. According to the American Psychology Association, the workplace continues to be a leading cause of stress (with 61% of Americans listing work as a significant stress factor).

We’re under more pressure to spend more time, to get more done every single day. Work-life balance has become a cliche joke.

While I believe in hard work, giving more of yourself than is asked in the job description and just kicking ass in general, organizational culture must be a fit to achieve our goals of world domination.

Here are three aspects of insurtech culture vital to success:

  1. Always put staff satisfaction first. An inspired team believes, an uninspired team blames.
  2. Never blame the customer. Period. Own your outcomes. The customer may not always be right, but the customer is never wrong.
  3. Don’t take yourself too seriously. As an old mentor used to tell me, “Everybody ?s.”

I’m sure there are more. But these were the three most obvious to me after spending time at the Bold Penguin headquarters this week.

7) Your Story Matters

Your story matters as much as your product.

It doesn’t matter how amazing, revolutionary or game-changing your product or solution is, if your story doesn’t make sense, if people can’t connect the dots between your solution and how it benefits them and their organization, your product essentially doesn’t exist.

This is something we need to do better at Bold Penguin.

We’re not amazing at telling our story today.

We’re going to change that.

One of many reasons I joined Bold Penguin was that the whole story had yet to be told.

I feel like I’ve found a gigantic diamond just lying there on the sidewalk.

And while everyone else walks past, oblivious to the treasure they’ve just nonchalantly stepped over, to the trained eye all it takes is a craftsman-like approach to telling the story of what Bold Penguin can do for insurance agents, brokers and carriers to unlock industry defining value.

But Bold Penguin isn’t alone. Wait until you hear about what Joseph D’Souza is doing at ProNavigator, or Jason Keck at Broker Buddha, or Phil Edmundson at Corvus Insurance.

Having a great solution is the barrier to entry. For anyone to care about your company, you must to be able to tell your story.

See also: Innovation: ‘Where Do We Start?’  

The Rub

According to the most recent CIAB Market Study, “Driving organic growth, hiring and recruiting talent and enhancing the customer experience remain top organizational priorities” for the U.S.’s top insurance brokerages.

With 80% of CIAB’s responding agents and brokers listing “driving organic growth” as a top priority for 2018, it’s exciting to be part of a company working to solve organic growth concerns, not through disruption but through collaboration, facilitation and integration.

You can find the article originally published here on LinkedIn.

Click here to learn more about Bold Penguin.

Talking Insurtech With Regulators

Key Points 

  • Recent shifts in insurance regulation are driven by consumer demand.
  • Traps for the unwary mean that insurtech startups should engage with regulators early and often.
  • Brokers need to know how to navigate the complex framework of anti-rebate and anti-inducement laws.

It is no secret: Investors are pouring money into insurtech startups with the goal of transforming the insurance industry. This increased investment is fueling not only growth in the industry, but also growth in the number of conferences, expos and seminars that allow companies to promote their products, build connections and stay abreast of the latest trends. Last month, more than 3,500 startups, insurers, investors, and service providers converged on Las Vegas for the largest and most global of such conferences: InsureTech Connect.

Attendees at this year’s event were treated to a host of presentations, from insightful fireside chats with entrepreneurs, such as Metromile’s Dan Preston and Ring’s Jamie Siminoff, to thought-provoking panels on satellite imagery, telematics, wearables and innovative strategies for insurance companies of the future.

See also: InsureTech Connect 2017: What’s New  

But, as excitement and buzz steadily mount, at least one panel reminded attendees that insurance—while highly ripe for innovation—is also a highly regulated industry. The panel (“Balancing Innovation and Regulation”) featured Michael Consedine (CEO of the National Association of Insurance Commissioners), Ted Nickel (Insurance Commissioner of Wisconsin) and Chris Cheatham (CEO of Risk Genius).

Here are our key takeaways of that panel discussion.

Recent policy shifts are driven by consumer demand.

Over the past 200 years, the insurance industry has gone through periodic changes. But, as Consedine explained, this is the first time that significant changes are being driven by consumer demand. Specifically, consumers are demanding simpler and more intuitive policies; a streamlined and digital application process; faster claims payments; mobile access; and new products, such as peer-to-peer or pay-as-you-go. Insurance regulators nationwide realize that innovation will lead to consumers being better served, and, as a result, they are taking an active role in being a part of the conversation and enabling innovation.

Traps for the unwary mean that insurtech startups should engage with regulators early and often.

Once a company begins to analyze risk or price products, it runs the risk of being considered an insurance company and, more importantly, being subject to a host of often complex regulations that vary from state to state. For instance, while the amount and quality of available data are exploding—opening up the possibility of using new or unconventional data to price risk—state laws prohibit not only unfair discrimination generally, but also specific factors from being considered when pricing risk. In other words, as Mr. Nickel explained, a data set may show that there are more pool deaths in years when a Nicholas Cage movie is released, but whether that correlation is actuarially sound, let alone a fair basis on which to make pricing or rate decisions, is something that companies should discuss with regulators before launching. The same is true with respect to other issues, such as privacy or cybersecurity regulations—companies should understand the regulatory regime in which they operate and ensure that they are in compliance. To that end, Mr. Nickel encouraged companies to engage regulators from the outset to explain how a new algorithm or business model works to ensure that they are not running afoul of state regulations.

If you are a broker, be aware of anti-rebate and anti-inducement laws.

Nearly every state (with the notable exception of California) has some form of anti-rebate or anti-inducement laws on the books. Generally, these laws prevent a broker from providing something of value to a customer to “induce” an insurance purchase. While promotional items, such as golf balls and pens, are often exempt from such laws, a company must be especially careful when it begins to offer—at no charge—more valuable goods or services to its customers. According to Nickel, these laws might be particularly problematic for new entrants into the industry. For example, if a broker provides a wearable device to its customers, might such a gift implicate anti-rebate laws? What about specialized software provided at no charge? New companies in the broker space should ask themselves these sorts of questions sooner rather than later, seeking out counsel when necessary to avoid regulatory issues down the road.

‘Tear Down the Information Silos’

Instead of a short bio, let us know what are your top three books everyone working on digital transformation needs to read and top three tech gadgets one needs to have?

“Zero to One.” This is the best book on tech, and so many entrepreneurs don’t understand the key concept: Your tech better be 10X better if you want to win,

“Moneyball.” I love this book because it helped me see how someone can look at a problem totally different. In the case of “Moneyball,” Billy Beane started looking at baseball stats in a different way.

“The Dip.” This is Seth Godin’s best book, and it’s super short. 10X better technology takes time. You will hit a new dip every single day. Pushing through the dip is key; 99% of people don’t get through the dip in some form or fashion.

iPhone. I hate my phone and love my phone all at once. I saw some crazy stat that it’s still a better deal at $1,000 than most gadgets, based on the number of times you touch it in a day (versus everything else).

Garmin Fenix 5. I was really disappointed with my Fitbit. So I ponied up for a Fenix 5 watch, and I absolutely love it. I love how well it is constructed.

Calendly (or equivalent scheduling app). I would go insane without this app. Seriously.

You are not only the CEO of RiskGenius but also a renowned influencer in the insurance industry. First, tell us more about your company. How far are you with becoming the Google of insurance?

We are getting closer every single day. Users can now use our Google-like search to find and compare policy language instantly. Now we are moving to an analytics based approach — put another way, the computers are going to start showing insurance pros what is and is not important.

See also: Why AI Will Transform Insurance  

When you start a discussion – for example, on LinkedIn – a lot of experts from around the globe participate. What role does social media play in your work as CEO? What would you recommend to C-suites of incumbents who don’t have an interactive presence on the internet?

Social media is our secret sauce. I have more than 100,000 followers on LinkedIn, and most of them are in insurance. That is crazy. I use LinkedIn to share wins, struggles and ideas. Some day, I would love to go back and read through all my crazy LinkedIn posts.

Most corporate social media is so, so boring. I love the personal touch. And, I guess you have to be a bit controversial — although I don’t really think my posts to LinkedIn are that controversial. For example, I recently posted that you can’t fix your front end until you address your legacy software. I don’t see that as controversial; others did.

Life is too short to be boring.

How do you estimate the state of the industry inside and outside the U.S.?

Honestly, we are in the first inning of a nine-inning transformation. There are major insurance corporations that are just now scanning in paper documents. Most insurance professionals can’t really find the digital information they need. We have so far to go.

What do you think are the biggest chances for incumbents to use the digital transformation? What are the biggest hurdles in your opinion?

The biggest opportunity and the biggest hurdle is tearing down information silos. I can’t tell you how difficult it is to get our hands on  an insurance carrier’s forms sometimes. This occurs because (1) the information is not stored in a central location and (2) the information gatekeeper does not want to give up the information to a more efficient system.

Herbert Fromme, maybe Germany’s most famous journalist on insurance topics, said a few weeks ago that insurers can reduce the majority of tasks in the future and, for the rest, need employees with different skill sets. What do you think about this?

Absolutely, and this is no different than most other industries. I used to be a litigation attorney. I attained my billable hours primarily by reviewing large document sets on cases. Two years into my career, I started reading about outsourcing operations that would review litigation documents at a fraction of the cost. Two years after that, I started reading about technology-assisted review, which involved machines reviewing litigation documents.

The same thing is happening in insurance. Insurance companies have just gotten comfortable outsourcing many jobs to other countries where labor is cheap. And now you are starting to see machine learning solutions that can do the outsourcing work (ahem, www.riskgenius.com).

What are your top three do’s and don’t’s for a C-suite that understands the need to act soon?


  1. Spend most of your time on the problem.
  2. Make sure you have buy-in from all employees — not just executives.
  3. Avoid reading traditional tech press — do your own research.

See also: How Technology Breaks Down Silos  

What would you advise young people who are thinking of entering the insurance industry?

Go get a job in insurance and pay attention to all of the crazy, frustrating situations that you see. There will be a lot. It is the nature of the beast. Talk to your peers about the problems you are having. See which problems others focus on. Then figure out how to fix the problem you have selected.

Thank you for your time.