Launching Sunthra: My New Project
June 2, 2025 | Issue #120
Big Deal Small Business: Launching Sunthra: My New Project
June 2, 2025 | Issue #120
This is a blog written by Kaustubh Deo // Guesswork Investing about acquiring & operating small businesses. If you are a new reader / new searcher, please start here.
Introduction
My personal mission is “To be a source of strength and stability for myself and for my people.”
Over the past several years, the SMB/ETA world has become a fundamental part of my people — and I intend for that to continue to be the case.
To me, strength means pushing my people to do more and think more deeply about their lives & relationships.
In a small business context, this means serving as a thought partner to searchers and small business owners — I want to help them craft their lives intentionally. I want them to proactively define success in a way that is specific to them. I do this primarily through my blog, podcast, and community-building activities.
Stability means being reliable. It means bringing a calming energy and helping contextualize or reframe difficult moments.
In a small business context, this means serving as a supportive investor and strategic partner. It’s about talking through a key hire or fire decision. It’s about giving a small business owner the support they need, both financially and emotionally, to get through tough moments.
That brings me to Sunthra — read on below.
Sponsor Information
Big Deal Small Business is sponsored by Live Oak Bank, a leading self-funded search fund lender.
To learn more, reach out to Lisa Forrest and Sarah Andrews at Lisa(dot)Forrest(at)LiveOak(dot)Bank and Sarah(dot)Andrews(at)LiveOak(dot)bank.
Mention that Kaustubh from Big Deal Small Business sent you!
What is Sunthra?
Marathi is my family’s native tongue — if you haven’t heard of it, you’d be surprised to know that it has 80+ million native speakers, ranking it 15th in the world (more native speakers than French or German). India is a big country.
Sunthra is the Marathi word for orange (the fruit).
My family has a deep background in orange farming — my great-grandparents were still alive when I was a child, so I got to visit the family farm during trips back to India. I’ve picked oranges straight off the trees and juiced them with my great-grandmother.
Given that context, there’s something fitting about the fact that I ended up acquiring a tree care company in Seattle. I’m now an ISA-Certified Arborist as well (passed my test recently).
If you haven’t noticed, my small business activities have grown to encapsulate quite the array, from this newsletter to happy hours to speaking to podcasts and more.
I’m preparing to launch a brand new initiative — more on that below, please be sure to read if you’re curious about investing in small business — leading me to take stock of my activities as a whole and bring them under one umbrella with an aligned purpose.
Sunthra is the name of my new entity that will serve as that umbrella.
Sunthra’s New Initiative: Syndicate Investing
I miss being a more active investor. I know I can be a good investor, and I know my investing activities will directly support SMB folks, operators and investors alike.
To that end, in partnership with Mainshares, I am launching a syndicate offering. Follow the link to learn how it works and to apply to join the list, but in brief:
You join my syndicate list as a prospective investor (must be accredited) — no commitment or requirement to invest.
I find & vet small business deals.
If I like a deal enough to invest in it, I share it out with my syndicate list to see if others want to invest alongside me.
You decide if you want to invest alongside me or not on a deal-by-deal basis.
I earn a carry fee on your investment if the deal goes well.
I’ve been reticent to take other people’s money in the initial years of my own business. I just haven’t had the bandwidth to underwrite deals the way I’d want to if I were investing other people’s money — it’s a much higher bar than my own money, frankly.
That has now changed for two key reasons:
My business is in a slow but steady grind as it compounds into a high-quality, larger business. It’s my full-time job & focus, but it won’t be helped by my adding an extra 10 hours/week on it. If anything, it’ll be helped by my engaging with other SMB owners & searchers.
I now have the bandwidth to underwrite properly. I have invested in five small business deals personally to date, and have developed enough of an internal underwriting framework to feel comfortable taking other people’s money.
To be clear, SMB investing remains a high-risk, highly-leveraged proposition.
But for an investor who is looking to invest alongside a seasoned SMB investor & operator (with PE investing experience before that), my syndicate offering could provide a good solution.
Lastly, I would note that you should not expect high volume from me — this is not my primary focus, and I will be highly selective on what deals I decide to pursue. Running a syndicate is not my primary way of making money…it likely won’t generate any money for several years in fact.
Feel free to reply to this email if you have any questions.
Searchers — I will be a more active investor going forward, targeting checks over $250K through my syndicate, so please feel free to reach out early in your search process. The investments I’ve made thus far have all been in searchers that I got to know before they had a deal in hand.
Other Activities
I’m excited to formalize my small business content & investing activities in one home, Sunthra. I appreciate all of you for following along and sharing your thoughts along the way.
Here’s the list of what I do at the moment:
I write Big Deal Small Business (this free newsletter) and Guesswork Unveiled (the paid version, for operators)
I co-host The Intentional Owner with Sam Rosati, a podcast about life as a business owner. You can find it on Apple, Spotify, or YouTube!
I run a monthly happy hour and community for searchers & business owners in the Seattle area. Email me directly to be added to that list!
If you’re a golfer, I’m planning an SMB/ETA golf trip for later this year in partnership with Bird Golf Academy — if you’re interested, please fill out this form as we are actively planning it right now!
You can also follow me on Linkedin…I’m slowing down on Twitter these days and posting more frequently on Linkedin.
Feel free to plug in wherever you find your interests overlap with mine!
Thanks,
Kaustubh Deo // Guesswork Investing
Hey! I saw your post pop up on my homepage and wanted to show some support. If you get a chance, I’d really appreciate a little love on my latest newsletter too always happy to boost each other!