Raghav “Rags” Gupta is an entrepreneur, operator, investor and author of the bestselling One to Ten: Finding Your Way from Startup to Scaleup. He currently serves as president of Butlr, a wireless motion-sensing platform that generates privacy-compliant, anonymous data for physical space management. Corporate real estate, senior living and wellness facilities, and retail spaces use Butlr to detect occupancy, headcount and activity, and generate accurate, real-time and historical spatial insights. Gupta is also a venture partner at Hyperplane.vc, and board member at Dvinci, in addition to being an active angel investor with TBD Angels.
Prior to Butlr, Gupta worked with dozens of VC-backed companies which achieved multiple exits. He was part of the founding management team at Brightcove, helping it grow to IPO; Chief Commercial Officer at Videoplaza, acquired by Telstra; GM EMEA at Ooyala; and COO at Humatics, the breakthrough microlocation startup.
You can listen to the Boston Speaks Up podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):
Where did you grow up? And how would you describe your childhood?
Born in India, grew up in Philly suburbs. Childhood happy overall — Indian kid fitting into American suburban life.
Who were your role models growing up?
Family members, teachers and, not sure it counts under "growing up," but most of all it’s been a professor in undergrad who opened my eyes to entrepreneurship.
What is the first career you remember wanting to pursue?
Started in management consulting and quickly realized it wasn’t for me. Got into tech after having taken a class on entrepreneurship as an undergrad.
To help out our younger listeners tuning into the show, can you speak on your internship experience(s)? In addition, can you share any insights you may have on the importance of internships/experiential learning (outside the textbook)?
I interned at a wealth manager and management consulting. Hugely important to do experiential learning. So many more opportunities to do that now than back then and take full advantage — robotics clubs, hackathons, etc.
Is there a particular person or event that helped shape the career path you took?
Ed Zschau and his entrepreneurship course at Princeton.
What is the biggest challenge you’ve overcome getting to where you are today?
It’s been getting over my own psychology.
How would you describe your leadership style? Have you learned any big lessons in your experiences leading others thus far?
Servant leadership. I’ve learned lessons from every person I’ve worked with and for. The biggest is to connect things back to the "Why?": Why are we doing this, why does what you work on matter?
What’s the most exciting part about being an entrepreneur?
The ups and downs of the journey make it exciting (and stressful too). The biggest reward is working with people you get along with to build something that impacts peoples’ lives
What do you find most exciting about the investing sector right now?
Covid has catalyzed so many to try something new. The opportunities out there are only accelerating. I also have a contrarian streak and get attracted to sectors that are no longer ‘hot’. For instance, last year I invested in onescreen.ai in the outdoor advertising space. Adtech/marketing tech isn’t trendy right now but it’s big and they’re solving a real problem.
What sorts of challenges and opportunities have you found in the pivot to virtual business and networking during the Covid-19 pandemic?
All the usual ones…the paradox is it can be easier to meet people and get access but harder to close meaningful deals and new relationships. We are all figuring this out.
Final question: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… what is one challenge you have for the listeners?
Give specific compliments to five people who may not be expecting it.
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