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  • Writer's pictureZach Servideo

071: Boston Speaks Up with Rick Grinnell of Glasswing Ventures

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.

Rick Grinnell is the Founder and Managing Partner of Glasswing Ventures, a venture capital firm that invests in pre-seed and seed-stage companies in AI and frontier software technologies. After an early career in marketing, Grinnell has been investing in security, storage and SaaS-based startups out of the Boston area for the last 21 years, becoming a staple in the local innovation scene. An MIT and Harvard grad, he’s also music-obsessed and a self-described tech nerd.

You can listen to our podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):

Pre-Podcast Q&A:

What role has music played in your life?

Music has always been my favorite creative outlet, going back to my childhood. I started writing songs when I was 5 or 6 years old. Playing music and composing is also a stress reliever, playing an important role throughout various phases of my life.

I learned how to play the keyboard (actually a theater organ) from my dad, who had a passion of playing every night after dinner. He was my early musical role model.

Over the years, my love of music, and particularly music and sound technology, led me to pursue EE at MIT. I thought I’d work in the music industry, or for a company like Bose, at that point in my life. So music set me up for my ultimate career in tech.

Where did you grow up? And how would you describe your childhood?

I grew up in Schenectady, NY, which at one point in time used to be the HQ for GE. My childhood was a somewhat “perfect” middle class upbringing. My dad was a high school teacher, my mom at one point was the same, but stopped working when I was born. I had a great relationship with my parents - they are still two of my very best friends in the world.

Who were your role models growing up?

My parents, for sure. My dad and mom were both hard workers, and as teachers they were so critical to my development. They exposed me to lots of great things - music, art, history, science, etc. at a very young age. We spent lots of weekends going to museums, performances, etc.

What is the first career you remember wanting to pursue?

A pilot! I still love planes.

To help out our younger listeners tuning into the show, can you speak on how your internship experience(s) OR first jobs growing up shaped the man you are today and the career path you’ve taken?

My first jobs growing up were musical - I was a church organist and in a wedding band. Both of those taught me the importance of practice and being prepared. The wedding band also taught me the importance of being flexible and gave me improv chops. You never knew what was going to happen, or what curveball you’d get hit with during the wedding. You could practice the bridge and groom’s set list for weeks before the wedding, and then have the bride’s dad or mom change everything on the day because they only wanted Frank Sinatra songs played.

My first relevant internship was at MIT, working for a professor doing research on cartilage regeneration. That experience was important to my focus on details. Just one small mistake could blow months of research.

And my co-op experience at MIT (working for GE’s R&D Center) showed me that big companies, even successful ones like GE - they were a Top 5 company at the time - weren’t for me.

How was your time at MIT? Do you have any connection to them any more?

MIT was amazing at a people level. Most of my best friends come from those days. And the professors were just great. I can’t say I loved the quality of life or the workload, but I survived with a high GPA and it opened a ton of doors. I still work as a volunteer for the Admissions Office interviewing applications. I love that!

Do you have any advice to young people trying to break into the VC world?

  • Do everything you can in college or in your current job that makes you more valuable to a venture firm. Network like crazy, research companies that are (or aren’t) in your field and interesting to you. While you don’t have to have a technical degree, you need to understand tech, products and markets. And find warm intros to get you in touch with the VCs that you’d like to work with. Work those connections. While you may not get a VC job right out of school, keep up the connection. And consider working for a portfolio company as a way into a VC firm.

  • Understand that the availability of jobs in VC is low, but the right operating career and success can improve your chances over time. Consider sales and marketing jobs as path to ultimately break in (or not.)

Is there a particular person/mentor or event that helped shape the career path you took?

A former PictureTel VP of Marketing, Steve Johnson, gets the credit for helping me get out of engineering and move into the business side of tech. He took a chance on me, and I will always be grateful.

What is the biggest challenge you’ve overcome getting to where you are today?

Hmmm. Hard one. Perhaps staying true to who you are and how you were brought up in an industry that oftentimes rewards those that have put financial success ahead of everything else.

Speaking on the topic of *dependent on previous answer*, what’s the biggest lesson you’ve learned from your experiences *dependent on previous answer*?

Stay true to who you are. Dollars and cents isn’t the only way to keep score in life.

Now, clearly leadership has and is still a large part of your career today, I’d love to know 1. How you would describe your leadership style? 2. How you got to that point? (Was it always like that?)

I’m demanding and blunt, but in a very friendly way. I think I inherited that from my dad, who was a tough teacher, but everyone’s favorite.

What do you find most exciting about the VC sector right now?

The amount of innovation that we are seeing in the AI world right now, and the amount that will continue for years to come. We are in the 1st inning.

What sorts of challenges and opportunities have you found in the pivot to virtual business and networking during the COVID-19 pandemic?

Challenges - team cohesion and training new employees. Cyber attacks have taken advantage of distributed teams. Harder to do diligence on companies remotely.

Advantages - I am twice as productive working remotely. Can do many more meetings in a day, and still have time left over to think, work on strategy, etc.

Of those, what do you think has changed forever? Maybe even has been a silver lining..

I’m not sure anything has changed forever in my world, but for at least some time engineering in particular will be conducted effectively remotely.

What are some of the most recent trends you’ve been seeing in the VC world? What do you believe will succeed in longevity?

Investment decisions being made very quickly - perhaps too quickly, particularly while doing diligence remotely. Will give examples. Pricing acceleration with more later stage funds coming down market to get in earlier.

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?

I have two - never stop learning something new, particularly a skill. Learn a new language, pick up the guitar (I started that a few years back), start kite boarding, etc. Just never stay stagnant on this side of your life.

And no matter how young or poor you are, find ways early in your life to give back. It doesn’t have to all be about donating. Become a Big Brother or Big Sister, work at the local food bank, etc.


You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting

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