Welcome back to The 2x2 - the ultimate newsletter for executive consultants!
How many people from your last networking event actually showed up when things got hard?
For most founders, the answer is nobody — and Sudeshna Sen carefully built an entire company around that problem.
Read on…
⏰ Today in 5 minutes or less:
Most founders are over-mentored and under-supported — and those are two very different things.
Shallow networks look productive. They just don't show up when it counts.
The consultants who build something lasting aren't the ones who moved fastest. They're the ones who listened longest.
WORK WITH ME
My firm Keenan Reid Strategies builds 9-figure business models and the financial engines behind them. We help enterprise B2B leaders:
MORE FROM THE 2X2
🔊THE PODCAST → Listen to the world’s greatest podcast for indie consultants.
📚 THE LIBRARY → Our full archive of content. Sign up FREE for a limited time.
💬 ASK ME ANYTHING → I share the unspoken rules of building a serious indie consulting practice. 👉 Got more questions? Drop them here.

Forget Hustle Culture. Here’s Why Being Intentional Wins.
We've always been told the same story about building a business: network hard, move fast, say yes to every opportunity.
Sudeshna Sen believed it too – until she left corporate and tried to build something of her own. That’s when she realized the playbook we know isn’t always the answer.
What she found, after slowing down and actually listening to the founders around her, was that the problem ran deeper than tactics. Women founders were surrounded by communities, events, and connections – and still felt completely alone when things got hard.
Not because the support wasn't there, but because none of it was real when it counted.
That gap is what Pionyr is built to close.
In this conversation, Sudeshna talks about what it really took to build something worth building – and why going slow was never the setback it looked like.
You said you thought you’d be in corporate for the rest of your life. What changed?
Sudeshna: I wouldn’t say it was one moment. It was more of a slow reckoning, and it took me years to get to that point.
From the outside looking in, my corporate career looked great on paper. I had a great title, big responsibilities, an amazing team, and I was doing well professionally.
But internally, I felt overwhelmed. I was always tired from the travel, the pace, and the lack of agency over my calendar. There was this constant exhaustion.
And I think the feeling had probably been there for a long time, but I wasn’t listening to myself because I was in so deep. What changed over the last few years was that I started paying attention to how I actually felt.
I realized I felt suffocated. In corporate environments, you often get stereotyped based on your past experience. People decide what kind of roles you’re “right” for. I started feeling boxed in creatively and professionally.
At the same time, I had started getting plugged into the startup ecosystem as a mentor and investor. I also tried building a few things on the side while still working full-time. That experience led me to be curious again.
Entrepreneurship brought me back to that part of myself. I feel like I’ve returned to that childlike curiosity again. And honestly, that’s been one of the most fulfilling parts of this journey.
Once you left corporate and started building Pionyr, you spent more time inside the founder ecosystem. What surprised you most once you were actually inside those rooms?
Sudeshna: How lonely many founders actually were. From the outside, the system looks incredibly connected. People are constantly networking, joining communities, meeting investors, and posting about it online. It’s like everyone has access to the support they need.
But once I started having deeper connections with these founders, I realized how isolated many of them felt – especially women founders.
Sure, they had mentors, advice, and people willing to tell them what to do. But very few had real support systems. And there’s a huge difference between advice and support.
I also noticed that many women founders didn’t feel psychologically safe in traditional founder environments. There’s always pressure to look confident and successful, like you know exactly what you’re doing.
But entrepreneurship is uncertainty all the time. That realization became the foundation for Pionyr.
It’s not just another networking community. It was built to be a space where women founders could actually feel supported emotionally, strategically, and practically – while they build their business.
What have you found women founders actually need most?
Sudeshna: Women founders need a space where they truly feel safe to be themselves. I think women entrepreneurs are over-mentored and under-sponsored. There are so many ecosystems designed around advice, but what founders really need is support.
They need somebody who is actually there when things are falling apart. Somebody they trust. Somebody who will help them move forward in the moment when things are breaking.
And despite all the networking events and startup communities that exist, I still see so many founders feeling deeply alone.
A lot of people spend time going to events trying to meet as many people as possible. Sometimes they work, but most of the time they create surface-level relationships. It looks productive because you meet a lot of people, but there’s no depth when you really need help.
You have finite time as a founder. If you spend all of it building shallow connections, you never create the kinds of relationships that actually support you through difficult moments.
That’s why intentional communities matter so much. When people genuinely help each other, when they invest in each other, the relationships become much deeper. Those are the people who actually show up when you need them.
You’ve talked a lot about building intentionally. What does that actually mean in practice?
Sudeshna: For me, it means moving forward with curiosity and resisting the pressure to rush.
It means saying no to shiny objects, or opportunities that might distract you from what you’re actually trying to build.
Even after leaving corporate, I had opportunities come my way, but I had to be intentional about staying committed to the thing I truly wanted to build. And honestly, building slowly helped me.
The version of Pionyr that exists today took time because instead of building what I thought founders needed, I listened to what they were actually telling me – where members were getting real value and the moments Pionyr could genuinely help them when nobody could.
That clarity only came from slowing down and listening deeply.
I also see founders putting enormous pressure on themselves to move fast — especially around fundraising. They think they need VC funding immediately. But I’ve seen so many founders make better progress when they focus on customers first instead.
I think founders sometimes forget that customers are the signal. If you focus deeply on solving a real problem for real people, the rest starts to align around that.
What We Can Learn from Sudeshna Sen:
Slow growth can build a better business. Pionyr was built slowly by listening carefully to what founders needed instead of rushing to scale. The best positioning comes from paying attention to repeated problems over time.
Start building trust early. Networking events often create surface-level relationships that disappear when things get tough. Better to focus on building a small circle of deep, trusted relationships that lead to real opportunities and support.
Customer matters more. Instead of chasing investors, founders who make progress are the ones talking directly to customers and solving real problems. If you spend way more time looking impressive and getting no results, it’s time to pivot to clients and their pain points.
Fix that. Live. With Clay + HubSpot.
Defining your ICP on vibes is a pipeline killer. In Build Your GTM Alpha, Clay + HubSpot for Startups walk you through a live build. Real prospect list. Real enrichment. Real outreach sequence. You don't leave with a plan. You leave with outbound running. June 18. 11am ET / 4pm GMT.

For a More Joyous Existence…
There is no power in these points.
Adding this to my morning affirmations from now on.


