Venture Leader Q&A – Insights From Entrepreneur Jitin Agarwal

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This Q&A is a great opportunity for you to learn what sets venture leaders, like Jitin Agarwal, apart from others. How do they approach and conceptualize a project? What is their risk tolerance? Are they made of different stuff than the rest of us mere mortals?

This interview contains a lot of great knowledge and best practices for anyone wanting to learn more about building a business from scratch.

Can you give us a brief summary of your background as serial entrepreneur?

Sure, I’d be happy to answer that. Oddly enough, I began my career in finance, but I quickly found that my true passion and interest was in all things related to products – design, development and launch. Realizing that this was what I wanted to do, I left my finance role and took a position in what is now an old-school tech company called Microsoft – but, back then it was the Google of its day. That is where I truly was able to freely explore my passion for products, product development and launching them into market.

After a long-ish stint at Microsoft where I was a part of a number of intrepreneurial ventures within the organization, I was approached with an opportunity to take my experience and build a new venture outside the cocoon of a large organization. I took it, with the thought that I was on a great trajectory within the organization and, if my small foray into a startup venture didn’t work, I could always transition back to corporate life… back into ”the belly of the beast”.

As fate were to have it, that never really happened. I went from that venture, to a series of other ventures in multiple industries and in multiple CxO capacities which ultimately led to my current role as a Venture Leader of an intrepreneurial startup within a Fortune 500 company. It’s almost like I’ve come full circle in 25 years. I’m doing what I love and what am good at, in an innovative place that encourages and enables me to do what I enjoy most.

What drew you to startups and what keeps you interested?

That’s a good question and in my opinion, ultimately the most important question for any venture leader. I fundamentally believe that entrepreneurs are wired a little differently than the rest of those in corporate America. It’s kind of like those first responders to a horrific accident or tragedy who run TOWARD the danger, while the rest of us run AWAY. Now, don’t get me wrong, I’m not claiming that all or even any venture leaders will run into a burning building, we’ll leave that to the fire fighters, but we all definitely have a stomach for sailing into uncharted seas without getting seasick.  

What I am saying is that a venture leader looks at risk and their career with a vastly different lens or filter than the average career corporate individual. The reason for this is fairly simple, the last thing a good corporate “citizen” will do to advance their career is look to take on a role in a group with an undefined charter, navigating unknown waters, with an unclear set of tools, in an unknown part of the market, with an unknowable set of products with which to compete, and do so for an indeterminate period of time. What is surely the ultimate nightmare for most of those working their way up the career ladder, a world with NO LADDER at all, is my preferred playground.

As such, what drew me to being an entrepreneur and working in startups is the incredible size and scope of the challenges associated with a venture’s journey. The very uncertainty from all angles is what thrills, excites and challenges me to exceed every expectation. Where others see risk and uncertainty, I see opportunity and promise. Call me crazy, and I’ve been called worse, but that is what I’ve seen as a common thread among entrepreneurs. The ever-expanding and nearly endless scope of challenges that arise in every aspect of the venture lifecycle, whether it’s the first time through or the tenth is what continues to keep me interested and light my fire. 

Why do you want to share your knowledge with others?

There are a lot of factors that are necessary to build a successful venture. A great idea, good timing, the right people, getting to market before the competition, having an understanding of what should happen at each stage in the venture, and a nice dose of luck certainly helps. I’ve been lucky enough to be involved in a few successful ventures and I feel like it’s my responsibility to share what I know with others; it’s a way for me to give back to my community.

The information that I provide is one ingredient in the recipe for success which I am happy to contribute. There are many things I’ve learned across my seven ventures, and I’ve often thought, “Gee wouldn’t it be nice if someone had told me that before I got started.” Obviously, there is really no such thing as an entrepreneur’s manual. In truth, every successful entrepreneur will tell you the same thing – they’ve made it up or figured it out as they went along. By succeeding and finding their way, they can now conclude that they are successful.

However, it’s interesting because many of these same folks will not categorize themselves as successful – they’ll often say they’re “still working at it”, whatever IT is. This response is normal and seems to be in the DNA of entrepreneurs. It occurred to me some time back that, as I’m not the only entrepreneur in the market, I may also not be the only one who would wish someone would share their thoughts and experiences to help others avoid making mistakes. So, I started this blog with the thought “WHY NOT?” and the response has been fantastic so far.  

What do you enjoy most about your blog?

I enjoy sharing information with others a great deal. But, more than that, I enjoy engaging with other individuals directly and doing what I can to help or motivate them. In particular, I really like investigating and exploring markets, technologies, use cases, industries and other areas in the marketplace where I haven’t gone before. I view it as my own personal version of the Star Trek intro theme – going where no man has gone before! My blog allows me to interact with lots of different people, doing lots of amazing things all across the universe, I mean the marketplace.

This is an incredible honor, challenge and opportunity. It’s an honor that I’m asked so often to serve as the objective 3rd party who can come in with a fresh set of eyes to see a problem differently from an organization. This different perspective often results in us collectively solving “unsolvable’ problems. The challenge for me is oftentimes I’m learning a great deal about something that I was previously unfamiliar with, like IoT, IoE, Machine Learning or AI. All of these areas that were previously unknown to me but are now comfortably within my wheelhouse of expertise.

Finally, the opportunity to work with all of these kinds of ventures allows me to see the interconnected nature of the market and what’s occurring within it. This gives me even more data for pattern recognition and the ability to make my observations and input more insightful. It’s like a virtual loop that continually self-improves. Or to keep with the Star Trek analogy it is a constantly evolving, improving and self-repairing scenario, kind of like the Borg – although without the evil or world domination undertones!

What is your favorite phase in the venture lifecycle and why?

That is a tough one! I think each phase has its own charms, excitement and energy. I enjoy establishing the venture, because it’s where you’re pulling it all together. You’re finding the core need in the market, validating it and then assembling the team and resources to tackle that problem. I truly relish the opportunity to build products, because that is the life-blood of the venture. Without a widget or thing or service, you’re venture cannot exist. Making the widget is an amazing process and an awe-inspiring one – especially when you get it right!

Market launch is also very exciting. I mean, come on! Getting out there the first time with your product – it’s kind of like going to battle – at least the modern day version of it. It’s absolutely thrilling! Finally helping customers succeed is the ultimate validation of everything that you do as a venture leader in a venture and often why one becomes an entrepreneur in the first place. What are you building a venture for – if not to succeed in market with customers?

That said, I’d have to say that my core passion lies in the “build product” phase. It’s where I cut my teeth early on in my career and where I excel. I’m at my best at the intersection of people and technology and, for me, that’s product design and development.

 What are some of the biggest mistakes venture leaders make?

That’s a great question and definitely one for a future blog. I’d say that, in my experience, the mistakes venture leaders make all stem from ignoring, missing, or incorrectly responding to a step or phase in the venture development lifecycle. For example, a common mistake is to assume that a great idea, without a proof of concept or a minimally viable product (MVP) that customers can see, touch or interact with, will win them over.

There are a lot of good ideas out there and one of the key things that separates the winners from the non-winners is EXECUTION. In my opinion, it may be truly the ONLY thing that separates them. There can be no better example of your venture’s ability to execute, then to have an MVP that you can take to market. A vision or an idea is a great and necessary thing, because it inspires your venture to do more and be more – but that has to translate into someTHING that you can take to market to succeed. So that’s an example of the kind of mistake an entrepreneur will often make.

I recently wrote a blog entitled The Four Phases of a Venture Lifecycle to clearly articulate and lay out what should be happening in each phase of a venture. The goal was to give venture leaders an understanding or a high-level road map of a venture’s lifecycles to help them understand what to focus on and when and, more importantly, to ensure they don’t miss a step. 

What are some of the key attributes that make a good venture leader?

I’ve already alluded to it earlier in this Q&A. In my experience, the SINGLE most defining differentiator of a successful venture leader is their ability to drive execution. At the end of the day, the venture represents the sum total of the efforts and labors of those involved in building and running it. The greater that total, the more valuable and successful the venture.

The job of harnessing, channeling and unleashing the potential of those people involved in the venture, ultimately resides with and is the purview of the venture leader. To be successful, they must possess the ability to get the most, the best, and the greatest out of their team, no matter the size, to ensure that they get their product or service to market as soon as possible. The ability to execute on the right things is what differentiates successful ventures from failures.

 Are you speaking at any upcoming events?

Yes. I am a frequent speaker. You can find all of my current speaking information here.  

I welcome your comments, questions, feedback and insights below or feel free to email me directly here. Please read and share all my blogs at

About this blog – The goal of this blog is to share my experiences, to capture and reveal valuable insights, and to draw from my serial entrepreneur-ship through 7 ventures over the past 20 years. I have encountered many impressive entrepreneurs along the way and I hope to share our collective experience with you to help teach and perhaps motivate you to launch your own B2B or B2C enterprise.

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