Become a Tree Expert: Interview with Jared Kaplan, Co-Founder and CEO of Indigo
I recently went one-on-one with Jared Kaplan, co-founder and CEO of Indigo.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Jared: I’ve had a long career as a tech entrepreneur, and I’ve gone down a lot of different roads to get to where I am right now as CEO and Co-Founder of Indigo – an AI-powered insurtech platform for medical malpractice insurance.
I credit a lot of my ambition and drive to the way I was raised. I grew up in the Midwest and I’m an identical twin. Going through my childhood and teenage years with someone to healthily compete with allowed me to maximize every ounce of my academic and athletic potential at a young age. My parents were strong role models who artfully balanced their dedication to meaningful employment with family dedication.
I moved to New York City after graduating from University of Michigan’s Ross School of Business and spent a decade working at Goldman Sachs and Accretive, a private investment firm. At Accretive, we incubated businesses, and this experience motivated me to start an insurance business – Insureon – which became the fastest-growing agency in P&C insurance. We ultimately sold it to Hub International and Bold Penguin. After leaving Insureon, I served as CEO of OppFi (NYSE: OPFI), an AI lending platform powering community banks that went public in 2021, and as CEO of Cadre – a venture capital-based real estate startup that facilitated access to commercial real estate investment for the mass affluent.
Throughout my career, I’ve found that success is most certainly not linear. I’ve made many mistakes, especially as CEO, but still have been able to find success, and I attribute this in part to the drive I cultivated in my early years as well as the way I lead my teams. I believe that if you lead with authenticity and candor, your employees can build greater trust in you and are more willing to give you a second chance when you stumble.
Adam: In your experience, what are the key steps to growing and scaling your business?
Jared: I’ve found that sustainable business growth is driven by attracting and retaining top talent, clear prioritization of the company’s top initiatives at every stage of growth, and leading with transparency.
Adam: What is your best advice on building, leading, and managing teams?
Jared: Top talent craves autonomy, clarity of what success looks like, and ownership of achieving that success. They also value recognition for their achievements, enjoy working with a like-minded team, and desire fair compensation.
As a leader, I’ve prioritized transparency, and one way I embody this is by setting clear goals of what a team should set out to accomplish and continuously measuring the team’s work against progress towards this. I also encourage teams and individual employees to set what I like to call ‘comfortably uncomfortable goals’ – meaning people should be stretched, but milestones should be achievable. Unrealistic goals are demoralizing to top talent. At the same time, it’s important that leaders accept constructive feedback. Constructive feedback is a gift, and you should reward those willing to push back thoughtfully. Prioritization is also key. Too many leaders rule by “and” instead of “or”. I have found maniacal focus on a handful of initiatives creates better outcomes vs. trying to do everything.
Importantly, creating a workplace where employees can have fun, work hard, and take pride in their work is paramount.
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Jared: Even though AI is nearly everywhere today, we are underestimating the power of AI. In addition, technology should be integrated across the entire organization, not just within one or two departments, and it’s important to be strategic in how you use technology as organizations can often do a lot more with much less than they might realize. Lastly, start-ups have a major advantage as they don’t have an incumbent cost base that can hold up the utilization of new technologies.
Adam: What do you believe are the defining qualities of an effective leader?
Jared: Effective leaders over-communicate with their teams, lead with authenticity and candor, and empower and align their teams so that they have the resources they need to be successful.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Jared: Over the course of my career, I’ve found that I’ve learned the most from either negative experiences or moments of failure. In that same vein, I’ve always clocked what I didn’t like about some of the places I’ve worked, and I have used that to help me build the kind of business I have at Indigo.
I’d also challenge leaders at any level to remember what it was like before you earned the seniority you have today. Could you tell when someone was spinning a story? Were you treated with disrespect? Act the way you wish you’d been treated in those moments.
Many leaders have a bad habit of becoming “know it all’s” over time where they stop listening to their teams and predispose a solution because it worked before. If you hire top talent, they are always closer to the actual work, and their word is typically gold.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Jared:
Become a tree expert. When you’re really in it while building and running a business, you may not be able to see the forest from the trees, but if you master your area of expertise, you earn the right to elevate by being a tree expert and become mission critical to the company.
Know your business inside and out. You need to understand the details of the economics of your company, how the business operates and key data points to build strong unit economics over time.
If you see something, say something. Speak up if you’re doing something that doesn’t make sense. Leaders aren’t always perfect and sometimes can push the wrong levers. The best leaders rely on their teams to say something when they believe it’s not the right path for the success of the business.
Adam: What are your best tips on the topics of sales, marketing, and branding?
Jared: Above all else, you need to develop a product or business that quantifiably creates value for the customer above that customer’s next best alternative. For a new company, rarely does that mean engaging in expensive, traditional brand marketing. That’s typically a fool’s errand when you’re first starting out and profitability matters.
Instead, look for creative and less expensive levers you can pull to gain visibility and traction. This could include investing in SEO, collecting and sharing customer testimonials, seeking out opportunities to speak and network at industry conferences, or developing a robust LinkedIn brand. Test, test, and test again to figure out what mix of tactics drive the highest ROI and once you’ve determined what works best for your business, double down.
Adam: What is the single best piece of advice you have ever received?
Jared: From my Dad: “Two wrongs don’t make a right.”
Adam: Is there anything else you would like to share?
Jared: Though I consider myself a technology entrepreneur and have worked across a variety of different industries, I have been able to leverage a similar playbook each time by seeking out “old school” industries ripe for disruption from “new school” technologies. This recipe increases the probability of building something that can steal market share quickly by creating material value for customers.
Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.
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