Anubhav Saxena of Season Two Ventures: “At the end of the day, bootstrapping and funding both bring their own benefits to the table”

At the end of the day, bootstrapping and funding both bring their own benefits to the table. There’s no one option that’s inherently better or worse off than the other; it depends on which fits your situation and goals better. From a finance point of view, having funding gives you more power to scale, but […]

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At the end of the day, bootstrapping and funding both bring their own benefits to the table. There’s no one option that’s inherently better or worse off than the other; it depends on which fits your situation and goals better. From a finance point of view, having funding gives you more power to scale, but it also comes with high stakes and a “grow or die” mentality. At the same time, you’re looking at a somewhat fixed horizon, where you’ll exit the market in 5 to 10 years. When it comes to bootstrapping, this makes it harder for you to scale your company, but while you might grow a little slower, you’ll have the advantage of owning and controlling the whole pie.

Founders are often faced with the nagging question of whether Fundraising or Bootstrapping is the best choice for them. What is better, having access to capital or maintaining full control over your vision and profits? What is preferred, to have the seasoned oversight of an experienced investor, or to plow forward with a disruptive and pioneering ‘can do attitude? Of course, every situation is different, but what standards can be used to help a founder decide? As a part of this series called “Venture Capital vs. Bootstrapping: How To Determine If Fundraising Or Bootstrapping Is The Right Choice For Your Startup,” I had the pleasure of interviewing Anubhav Saxena, CEO of McLaren Strategic Ventures and Operating Partner at Season Two Ventures.

Anubhav Saxena, CEO of McLaren Strategic Ventures and Operating Partner at Season Two Ventures. From 2017 to 2020, as EVP and Chief of Global Alliances of Automation Anywhere, Anubhav has significantly contributed to creating the world’s largest intelligent automation and the fastest growing tech category. Led P&Ls on global vertical and horizontal sales, business development, channels, OEMs, ISVs, and other growth levers, including new geos, private equity sales, strategic alliances that powered a bootstrapped Silicon Valley start-up to a global 6.8B dollars valuation icon, with software deployed in 121 countries.

Thank you so much for doing this with us! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Exploration, experimentation, and innovation; my story began a little over two decades ago, through outsourcing leading massive digitization and transformation of the Indian subcontinent. We took it global, with efficiency and economics through Wipro Technologies.

Soon after that, through HCL Technologies, through offshoring, we brought massive technology and services efficiency and effectiveness by deploying global workforces that shifted the nucleus of work, workplace, and the workforce. A decade later, in ISG, advised G2000 enterprises to sustainably build IT workforces to support mission-critical businesses through the hybrid sourcing of technology & services. Half a decade ago, taking a bootstrapped robotic process automation company, Automation Anywhere, to becoming the largest well-funded intelligent automation company in the world while creating a hyper-automation economy and a world of human and digital workers.

A story that isn’t different from the four industrial revolutions we’ve seen or how various industries like manufacturing, textiles, and automotive went through outsourcing, offshoring, hybrid sourcing & automation. When capital, operations, and technology come together in unique ways with a powerful investor-operator mindset, we race to a digital future as we work to address society’s most significant needs. This helps define the future of work, where everyone wins. That’s been the inspiration behind my choosing this career path.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or takeaway did you learn from that?

Absolutely! I still remember it like it was yesterday. On the first day, being recruited first by the first multinational corporation that came for campus recruitment was considered the highest honor after graduating from our engineering college. Being the first one to be chosen gave you a sort of premium status amongst everyone you knew. And that selection meant you opted out of other opportunities on day two & onwards. While I was fortunate enough to be that on day one, little did I consider what role I took and recruited for, in which department, and for which location.

Getting the first possible position made me overlook the best choices I could have taken. They were there in the taking, only if I’d considered and evaluated carefully. Instant gratification, while it can build motivation, may not create lasting momentum. Prioritize and carefully choose with disciplined focus, and you’ll likely get the highest honor. That’s always more sustainable over time.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Integrity, accountability, and empathy are the three character traits that are a bedrock for being a successful visionary, strategist, influencer, operator, facilitator, decision-maker, and team player. While the human, economic, and social motivations for various actions might be different, we’ve always prospered when we’ve come together, dreamt together, and delivered together with integrity and accountability. Life’s experiences teach us the most challenging lessons, but with empathy, you get work, luck and a few prayers answered that catalyze new beginnings, inspiration. Empathy gives your dreams a chance. If what’s in your dreams wasn’t already inside of you, how could you even dream it?

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

Yes! While interning as a defense scientist on surface-to-air missile launchers, I was offered the opportunity to work on advanced technologies, which were emerging, new, untested, and took relentless effort, time, and sleepless months of experimentation. It was easier to give up and call it quits, choosing other safer career paths as most others did. It wasn’t till I realized the higher purpose of what was being attempted here. While creating new categories of innovation to defend, protect, and secure the country’s borders, we created unbounded economic, social, and human progress. It was my first tipping point in my career, and I learned that connecting work to a much bigger purpose would lead to success. Understanding how responsible action and innovation can unlock human potential and create sustainable businesses tied to a higher purpose has helped create millions of jobs and companies of multi-billion-dollar revenues that have continued to pay forward in the past two decades.

I believe that for a well-defined higher purpose, the world reorganizes itself to provide the strength and resolve to make it happen. It comes to you. This experience defined me and made all the difference.

None of us are able to achieve success without some help along the way. Is there a particular person or mentor to whom you are grateful who helped get you to where you are? Can you share a story about that?

It takes a village, and I’m always grateful to have had a tribe. It’s never one person. Every interaction is a round of evaluation that makes you who you are and helps you be better than you were. I’m grateful to all of the mentors I met, for they taught me in ways they’ll never know. I didn’t plan to meet them, but from all of them I met along the way, I learned and got the help, support, and guidance I never expected. I am so thankful for all they did and didn’t do, as it made all the difference. They’ve come to me as angels, dressed as ordinary people, leading everyday lives, helping me get through extraordinary circumstances and accomplish everything. For all those who’re reading this, you know who you are, you know what you’ve done, and you see the difference it continues to make. For that, I thank you.

You have been blessed with great success in a career path that many have attempted, but eventually gave up on. Do you have any words of advice for others who may want to embark on this career path but are afraid of the prospect of failure?

Every career path chosen and well done is successful. Are you working at the company that’s the best in what it does? Are you counted amongst the best in that company? Does the opportunity provide you, individually, to get a higher than expected economic, human, and social outcome? Have you identified the optimal ecosystem partners and cultivated the best team that will partner with the highest level of accountability, integrity, and empathy? And lastly, have you created the right environment and gathered the right tools to succeed in achieving your goals? If truthfully answered in the affirmative, the answers to these five questions would lead to unlimited successes.

Ok, thank you for that. Let’s now jump to the main part of our discussion. Can you share a story with us about your most successful Angel or VC investment? Or an investment that you are most proud of? What was its lesson?

Absolutely! Some of the most successful investments have been the ones that have contributed and returned well across all metrics, but primarily human, economic, and social dimensions.

These are founders and teams that I’ve met, known, and admired for their passion and contribution to the world. Some ventures include technology, warehousing, logistics that provide 10 million PPE kits, essential medicines, and groceries during the pandemic. Telemedicine, access to medical travel for senior & underserved communities, and even delivering mission-critical environmental intelligence for a healthier world are among my successful investments.

Others include my work with an educational learning AI/ML platform that enhances the quality of education and learning; another focused on data science for healthcare management, or my partnership with a Big 6 firm to deliver the world’s best cognitive compliance solution to maximize human contribution. Another is a recent New York-based investment that hires from underserved communities to provide the highest level of digital transformation to the most mission-critical financial services institutions, to another asset that makes financial inclusion possible. The lesson has to be finding them, walking with them, staying with them, and learning from them. I always hope to come, dream and deliver together with these ventures throughout the value creation process.

Can you share a story of an Angel or VC funding failure of yours? What was its lesson?

Failure is a teacher & its lesson(s) are extremely valuable. Very early on, I’ve invested time & capital in assets with unclear missions and vision, and I didn’t put together strategy, tactics, actions, and measurements that drove the teams cohesively. This created a lack of alignment. The team members were individually brilliant but collectively mediocre, with insufficient communication about their roadmap and results. The inability to put a sound ecosystem distribution model coupled with lack of buyer access, business development, customer success, and an inefficient capital model allocation led to a future of sub-optimal outcomes.

In the value chain, value creation is a work of science and art. Defined and executed well, it can increase one’s chances of success and the outcomes that are so richly deserved. Accountability, integrity & empathy across every function and department, along with transparency, are essential.

Is there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that story?

Of the many mistakes I’ve made, and yes, there are more than I could ever count, the few I remember are personal investments. I wanted to invest in a potentially game-changing health tech startup that established a chain of dialysis micro-centers to revolutionize the availability and delivery of dialysis therapy. The other was a tech-enabled start-up that facilitated a “farm to table” orders of fresh fruits and vegetables delivered directly to one’s doorstep. The investment thesis wasn’t to get a return — it was to fund innovation in the health tech and food tech industry and solve for health and hunger for millions. The other was a potential investment in a startup for a multilingual conversational AI Platform to employ the next billion in underserved communities and minorities. But the investor mindset in me overcame the purpose, and I engaged in commercial negotiations on terms, returns, preferences, and rights, overlooking the human reason that put me there in that investment position in the first place. When I didn’t get what I was negotiating for, I walked away.

The lesson is to stay true to why you do what you do and do it. Never mix the purpose, ambition, and goal.

Super. Here is the main question of this interview. Let’s imagine that a young founder comes to you and asks your advice about whether Venture Capital or Bootstrapping is best for them? What would you advise them? Can you kindly share “5 things a founder should look at to determine if fundraising or bootstrapping is the right choice”? If you can, please share a story or example for each.

  1. Choosing between funding through a VC firm and bootstrapping has a significant impact on how you structure and run the company — so this is a crucial decision. The pros of bootstrapping are that it allows for multiple pivots and retained control over one’s decisions over a higher timeframe. But this means you’re also contending with limited financials, which means fewer resources, potentially slower growth, and the risk of running out of capital and time. Funding provides more capital, which allows for more resources. However, you’re bound by rigid timelines and usually a limited decision-making ability, with less influence and inefficient financial discipline, as you give up efficiency for speed.
  2. It comes down to the end game and decisions to be made. The goal: to exit or not, and by when, with regard to the potential for growth and access to the resources needed for control. If you’re in a time-bound, highly competitive “winner takes all market,” this means that you’ll have to scale as fast as possible and maintain your position as the dominant player. This most likely means that you won’t be profitable in the near future and will need investment to afford your growth. If you’re in a fragmented market where many mid-sized firms co-exist, then funding may not be necessary. Under these circumstances, you might be able to bootstrap and grow it yourself.
  3. At the end of the day, bootstrapping and funding both bring their own benefits to the table. There’s no one option that’s inherently better or worse off than the other; it depends on which fits your situation and goals better. From a finance point of view, having funding gives you more power to scale, but it also comes with high stakes and a “grow or die” mentality. At the same time, you’re looking at a somewhat fixed horizon, where you’ll exit the market in 5 to 10 years. When it comes to bootstrapping, this makes it harder for you to scale your company, but while you might grow a little slower, you’ll have the advantage of owning and controlling the whole pie.
  4. The good news is, even though you don’t raise funding now, it doesn’t mean you have to be bootstrapped forever — it’s possible to raise funds later on in the game. (You might even get a better valuation for your company if you raise funds later when you’ve demonstrated your product-market fit and/or profitability!). So it comes down to goals, choices, your context, and terms.
  5. Personally, I would ask myself a couple of questions: If I can afford the resources and time to get to 2m dollars+ ARR without funding and then use the cash flow of the business to get to 10m dollars+ ARR without funding without losing position, time, leadership opportunity, I’d go bootstrapped, avoid dilution, hit my escape velocity and raise nine-figure valuations. That’s how I’ve done it in the past and that’s how I would do it again, every time.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

You’re too kind. It would be the “One Gratitude” movement. Every day, pass along your gratitude to one person and tell them what you admire about them and how they’ve helped you. Remember that at some time in the past, someone gave you a lift or an idea that started you in the right direction. Each of us can look back on someone whose simple acts of caring changed our lives, not only by teaching us but by taking the time to be with us and to believe in us.

If possible, also try to volunteer for a few hours a week. If every American did that, it would equal the labor of twenty million full-time volunteers. Each of us has a unique gift, and that should be paid forward.

Through McLaren’s Do-Good Initiative, we hope we’ll play our part and pay it forward.

We are very blessed that a lot of amazing founders and social impact organizations read this column. Is there a person in the world with whom you’d like to have a private breakfast or lunch, and why? He or she might just see this. 🙂

Yes, you have worked very hard to build a reputation, and following that read this column. Congratulations on your continuing successes! I’d like to meet and learn from fellow founders, entrepreneurs, and social impact organizations that empower leaders to leverage exponential technologies to positively impact billions of people. If you’re embarking on a mission, pivoting, or scaling to solve for that create a just, sustainable, and equitable future, I’d love to know you and be helpful and useful in my own way. Our “Entrepreneurs First” philosophy, available at, and desire to accelerate possibilities inspires us every day. And to know you, and partner with you; we standby.

How can our readers further follow your work online?

Please find me on Linkedin:

You can follow our progress at McLaren Strategic Ventures:

I’d be very interested in learning about your contributions, your mission, and how we can be useful and helpful to you and your purpose.

Thank you so much for this. This was very inspirational, and we wish you only continued success and good health!

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