When I sat down with Adam Crandall for this episode of Sunny’s Silver Linings, I knew the conversation would be valuable, but I didn’t expect it to feel like looking into a mirror. Adam isn’t just a founder and CEO; he’s someone who has lived the accidental entrepreneur journey the way so many in our MSP community have.
And what struck me first wasn’t his success. It was his mindset.
Here is a leader who has built multiple companies: from consulting firms to craft breweries to Benji Pays. He still speaks with the humility of someone who knows he’s still learning. That always resonates with me.
Lifelong learning isn’t a slogan; it’s the quiet engine behind sustainable growth. Adam even mentioned one of his favorite takeaways from Build IT: the “3 Ts” – Tools, Templates, Training. His team hears this a lot because he knows repeatable excellence doesn’t happen by accident.
Leadership Starts with Mindset, and Vulnerability
One of the first things Adam shared was his belief that leadership isn’t about the loudest voice in the room or the stereotype of the “chair-throwing” visionary. He talked about connecting with people at a personal level, showing vulnerability, and being willing to learn from everyone around him.
That openness… that humanity… that’s the foundation of great leadership.
I’ve always said: Growth mindset is the only mindset that has no expiry date.
The leaders who grow continuously, quietly, and courageously, are the ones who build something that lasts. And Adam embodies that.
He also spoke authentically about blind spots: something every entrepreneur has. His point was powerful: our blind spots remain blind until someone helps us see them. Great leaders help their people discover those gaps and their potential.
Culture Isn’t a Poster; It’s How You Show Up in the Trenches
When I asked Adam to describe the culture at Benji Pays in just a few words, he smiled and said:
“Get Stuff Done.”
GSD.
But the part that mattered most was what he said next:
If you want a GSD culture, your team must see you in the trenches with them.
He doesn’t ask anyone to do something he wouldn’t do himself.
He doesn’t preach ownership from a mountaintop.
He practices it: side by side with his people.
That’s leadership by design.
And yes, culture is collaboration. Culture is blind spot awareness. Culture is helping each person stretch beyond what they think they can do.
A team becomes high-performing not because of lofty speeches, but because of consistent actions.
Cashflow: The Reality Every Entrepreneur Must Face
Now, let’s talk about something that’s not glamorous, not inspirational, but absolutely essential: cashflow.
I tell this story often because it shaped who I am. There was a time earlier in my entrepreneurial life when I woke up every morning with knots in my stomach. Not because of customers. Not because of employees. But because I was running an MSP with tight cashflow.
Someone once told me:
Revenue is vanity.
Profit is sanity.
Cashflow is reality.
And that line stayed with me forever.
When Adam talked about why he built Benji Pays, it wasn’t from a product pitch mindset; it was from lived experience. He has seen how cashflow kills small businesses not because they aren’t profitable, but because money isn’t in the bank when it needs to be.
He shared the story of an MSP partner who never realized they had a cashflow problem, of course only until automation fixed it. Suddenly they had options:
- Buying a building
- Entering new markets
- Growing the team
Not because revenue changed.
But because cash started showing up on time.
That is the difference between entrepreneurial poverty and entrepreneurial creativity.
And for so many MSPs, especially those of us who started as techs rather than trained business operators, cashflow becomes the silent killer. We learned how to fix servers, not how to fix balance sheets.
If You Don’t Manage Cashflow, You Become a Bank: An Unpaid One
I shared a story with Adam about a friend who turned $2M into a $10M business simply by putting his money to work: not by selling time, not by selling labor, but by letting money make money.
Most MSPs unknowingly do the opposite:
They let their clients’ delays turn them into the bank.
If you’re collecting late, offering free credit, or sitting on 60- or 90-day receivables, you’re not an MSP…
You’re a bank. A bank that doesn’t charge interest.
A bank that takes all the risk, all the stress, and gets none of the reward.
That is not smart entrepreneurship.
And it is not responsible leadership.
Because here’s the truth:
You cannot be a culture-first company if your cashflow is starving your future.
Your team deserves a leader who builds financial security.
A stable cash foundation is what allows culture to thrive, not the other way around.
And Adam made another point MSPs often overlook: even if your P&L shows 20% EBITDA: a number many MSPs strive for. Slow collections quietly erode the real return on your business. Cash stuck in accounts receivable is the value you can’t deploy.
The Flywheel: Capability → Cash Confidence → Courage → Growth
This conversation with Adam reminded me of a principle I live by:
Be ambitious about your capability, not your cash.
Because capability creates value, and value creates cash.
When you automate cashflow (with tools like Benji Pays), something powerful happens:
You become cash confident.
And cash confidence gives you the courage to build more capability.
Which creates more value.
Which creates more cash.
That is the flywheel of entrepreneurial freedom.
One Thing Every MSP Should Do Tomorrow
Adam ended our conversation with something simple yet incredibly actionable:
Know your DSO: Your Days Sales Outstanding.
How many days does it take to turn an invoice into cash?
If it’s 60 days, you have a problem.
If it’s 30 days, you can improve.
And the best MSPs? They’re in the single digits.
Because cashflow isn’t a mystery.
It’s a practice.
And it can be automated.
He encouraged leaders to take even half a day and map their entire cash collection process. Find the bottlenecks. Spot the friction. Then automate the happy path. Free your people from low-value collection work and let them focus on meaningful contribution.
We Owe It to Our People to Build Cash-Healthy Companies
Entrepreneurs sacrifice so much: their time, health, sleep, family moments, all in the pursuit of building something meaningful. As Adam and I discussed, many of us didn’t go to business school. We were accidental entrepreneurs: waking up “unemployed” every day and building our livelihood from scratch.
But sacrifice alone doesn’t build a future.
Responsibility does.
Capability does.
Cash discipline does.
If you want to be a plus in the lives of your people, your customers, your family, then becoming a cash-smart entrepreneur is non-negotiable.
Adam and Benji Pays aren’t just automating payments.
They’re helping entrepreneurs shift from stress to creativity, from scarcity to stability, from surviving to designing.
And that’s why this conversation mattered so much.
