Putting down roots #ScaledFoundersRetreat
It took me a minute to take my eyes off the banyan tree. There it stood, strong and silent. Its roots were everywhere, snaking deep into the ground and cascading from the branches. What was once a dot-sized seed has turned into this spectacular provider of shade today, so grounded and yet so linked. It put me in mind of the nourishment, interconnectedness, and growth that it takes to live a meaningful life on Earth.
A nudge from my friend and SaaSBoomi volunteer, Ashwini Asokan, snapped me out of this spiritual trance the tree had me in. We were at a beautiful resort in Bangalore which is also quite easily accessible from Hyderabad if you were to drive.
The green sweep of this resort holds a special place in my heart. Seven years ago, founders had gathered at this exact venue for the exact same event for the exact same reason. Since the time we launched PNGrowth, nothing has changed and everything has changed.
In 2016, we had brought together founders in the same room as young first time entrepreneurs for the 2nd edition of PNgrowth, 35–40 in all, and encouraged the more successful ones to help the cubs find their way. Everyone split into groups based on their particular expertise and ambitions — those who had successfully pitched to SMBs in Southeast Asia were walking through those who wanted to follow them, others who had broken into the American SMB market were taking questions from a table of founders hoping to do the same.
The founders not only opened their playbook but also the decks they had made for investors, their spreadsheets, their board composition, their captable. Nothing at the time was untouchable. I remember standing at the back of the room amazed at not just the candidness but also the camaraderie. And everyone in the room was paying close attention, asking questions, finding details that I couldn’t even spot.
It is now seven years later, and the enthusiasm has not changed. This time around I spotted a familiar face across the room. This is a founder whose company was making about $500K-$1 million in ARR when he walked in to get ideas at the first PNGrowth. He is back this time having scaled the business to beyond $50 million, now ready to impart his own insights to the crowd as a mentor to a new set of mentees. It is like looking at the banyan tree again — SaaSBoomi is also defined by nourishment, interconnectedness, and growth. This is what pay-it-forward looks like in action.
At SaaSBoomi, our ambition is to encourage people to open their hearts just as much as they opened their playbooks.
It’s about heart
Scaling up can be just as lonely as starting up. So at this retreat, we decided to switch things up and debut a new format. We had scaled founders at a playbook roundtable where they deliberated on common problems that can crop up on the path to growing, and all the potential ways out of them. It is a slightly older group, with an average age of 38–40, rather than 30–32. I realise we think the older the founders, the less help they need but that is not entirely true or fair. The sessions are proof, they stretch over two days and revolve around questions that mid- to late-stage founders have to tackle, and the energy is as cracking as if they were first-timers.
Founders discussed hard business points as they broke down how to crack enterprise GTM and organisational design, but they equally also discussed soft skills such as managing the board and work-life balance. At times, a single slide inspired 90 minutes of Q&As.
There was one two-hour session where no one took a break. Not to drink water, stretch their legs, take a call, nothing. They sat there: listening, learning and contributing. Even when the particularly technical aspects elude me, I find myself still glued to the conversation because something in the air at those roundtables is magnetic.
That magnetism, I have figured, comes from the spirit of the community. When you learn that others have gone through or are going through the same troubles, the road looks a lot less intimidating. Founders perk up, their eyes shine with ideas, they smile more. It is the kind of experience that can bring a sense of kinship even among competitors. When I was planning the event, one of the founders was reluctant about opening their playbook because a rival founder was going to be in the room as well. But the spirit of sharing took over. But not only did the founders of both companies come along and deliver their respective talks, the next day they had put any insecurities behind them and as they bid goodbye they embraced each other.
All SaaSBoomi events are about acceptance. This is important for entrepreneurs who go through big highs and lows in the course of a single day — an investor may agree to back you just a few hours before an employee you groomed selflessly decides to chase another opportunity. Whether or not the money flies in, they have questions flying in from all sides — from customers, investors, family members, even themselves — about the health of the business or the rationale behind their decisions. But in the company of other founders, they can find answers, acknowledgement, and laughs. That can be pretty healing.
When the next retreat comes around in six months, we will be at this very resort and under the same banyan tree again. It is a proud moment to see the roots the community has put down and how strong they are getting.
