There is a future that I want General Catalyst to help create. It’s a future where inclusive capitalism prioritizes impact plus returns and is a mechanism for enduring positive outcomes. 

That future is our North Star. Yet I don’t know how to get there. And that’s the way it should be.

Our company knows that the route to the future we seek will be winding and unpredictable. It will depend on countless factors such as advancements in technology, changes in the political climate, shifts in the global economic ecosystem, and public opinion. We may at times go the wrong way or stall, and at other times we might catch favorable winds and race along faster than expected. But successfully navigating such ambiguity is what is valuable—more valuable than making a prediction about the future and “knowing” how to get there. 

Ironically, I often get credit for accurately predicting the future because General Catalyst invests in non-obvious company ideas that don’t seem to fit any pattern, and many of those companies end up creating a future most didn’t anticipate. But this happens because I don’t pretend to know the future. I can see the big problems to solve today, and I know that if a particular company solves one, that company has a good chance of becoming a significant success. But I don’t predict exactly what that solution and future will be like and push for the company to produce it. The future doesn’t unfold that way. Instead, I look for a founder or company that has a soul pointed at a big problem, and I look for the intelligence and passion and beginner’s mind that will help the company steer through ambiguity, always watching for new directions and opportunities that will help bring about the believed-in future—or an even better future that no one could have imagined. 

I’ve been learning about this principle over and over throughout my life. It started when I was a student at MIT. I didn’t go in with an idea about what I wanted to be when I grew up—like, Oh, I want to be a great academic at MIT—and work backward to plot a path to get there. Instead, I followed my curiosity and learned to be a lifelong learner, which would help me gain the capability to navigate ambiguity. I didn’t fully realize what I was doing at the time, but when I look back, after college that mindset allowed me to zigzag through cofounding a company, through my early years as a venture capitalist, through leading General Catalyst, and, now, through working to reinvent healthcare, energy, and other big sectors. 

Even now, I get reminded about the value of navigating ambiguity to solve a big societal problem. When I cofounded Livongo with Glen Tullman, we only knew that diabetes was an enormous problem that had mostly bad solutions. We didn’t—couldn’t— predict what the right solution would be, but we knew that if we applied technology and creative thinking, we would eventually find a great solution. Glen had the soul I was looking for. He’d already been CEO of a healthcare tech company, Allscripts, taking it public at a two-billion-dollar valuation. He and I both invested in medical-data company Humedica. So he knew and cared about healthcare. He also has a son and mother who have diabetes, so he intimately knows that the healthcare system is bad at helping people who have diabetes manage their condition so they can live a reasonably carefree life. Livongo was launched in 2014 with a soul, an important purpose, and a beginner’s mentality. At first, we experimented and hit dead ends. Over time, a new future started to take shape. We could give a patient a smart glucometer that would feed data about that person’s blood sugar, medical condition, activities, lifestyle, and eating habits to artificial intelligence software. The software, backed up by human medical professionals, would come to understand each individual’s diabetes and guide each patient like a guardian angel, working to keep the condition at bay. 

The future isn’t about having people with diabetes see more doctors and get more tests. It’s about helping each person manage the condition so they see as little as possible of doctors and get fewer tests. By navigating ambiguity, a better future than we’d imagined appeared. The digital health sector came to believe in that future, too, and Teladoc Health bought Livongo for $18 billion. 

By the way, Livongo’s outcome showed me another lesson about navigating ambiguity. We started Livongo to change the healthcare experience for patients. We thought we could get to a better future by starting companies that would disrupt an old way of doing things. But trying to change something as complex, enormous, and entrenched as healthcare from the outside doesn’t work. When we sold Livongo, it was treating about 500,000 diabetic patients. There are more than 30 million people with diabetes in the United States alone. While in certain ways Livongo was a huge success, it fell far short of General Catalyst’s long-term goal of reinventing the healthcare experience. But we learned a lesson, and after selling Livongo our company decided to pursue an unconventional strategy for reinventing healthcare: We’d partner with major healthcare incumbents, buy a hospital system, and together with the system invent products and services that will change the healthcare experience. No venture firm had ever done anything like it. But by navigating through the ambiguity, we saw a different path that could lead us to our desired future. (The process also led us to fully embrace the seventh principle in this book: For great change, radical collaboration beats disruption. I’ll explain more about that principle later.) 

Navigating ambiguity with a beginner’s mind took us to a different future than we had imagined. The future didn’t dictate our path; instead, the path created the future.

Excerpted from The Transformation Principles: How to Create Enduring Change, Matt Holt Books, September 23, 2025.

Author(s)

  • Hemant Taneja is the CEO of the global investment and transformation company General Catalyst.

    He is a nine-time Midas List investor, a best-selling author and a founder. His career includes early investments in market-leading companies like Stripe, Samsara (NYSE: IOT), Snap (NYSE: SNAP), Gitlab (NASDAQ: GTLB), Grammarly, Gusto, Applied Intuition, Anduril, Ro, and Canva.

    He has also hatched numerous companies like Commure, Tendo, and Livongo, which was acquired by Teladoc in an $18.5B merger, the largest in digital health history. He serves as the Founder and Chairman of the Health Assurance Transformation Company (HATCo) which works closely with several major health systems worldwide to drive their transformations. HATCo announced its intention to acquire Summa Health, an integrated health system in Akron, Ohio, in 2024.

    Hemant started his career as a founder, building a small mobile software company that was acquired, before joining General Catalyst as an entrepreneur-in-residence in 2002. He found his passion as an entrepreneur serving entrepreneurs and has been with GC investing and building companies ever since. He holds five degrees from MIT: M.Eng. EECS, S.M. Operations Research, S.B. Biology, S.B. Mathematics, and S.B. EECS. And he is a proud husband and father to three kids.