RelationshipOps of the Week #33.
Agency Advisory Firm
|
Jun 5, 2026
“No funnel. No pitch. Just trust, built over time.”
“No funnel. No pitch. Just trust, built over time.”
Steve Guberman.
This week, we’re spotlighting Steve Guberman, an agency growth coach and M&A advisor at Agency Outsight, a relationship-first advisory firm that helps founders scale, strengthen, and prepare their agencies for acquisition. He’s also the host of Agency Bytes, the go-to podcast for agency owners.
But Steve isn’t just another coach cheering from the sidelines.
Before launching Outsight, he founded Fifth Room Creative… a boutique agency named after the fifth room of his own home, where he felt the most creative. That firsthand experience as a founder shapes everything he does today. He’s not guessing the pressures agency owners face. He’s lived them.
What truly sets Steve apart isn’t just his frameworks.
It’s his philosophy.
He believes relationships are the foundation of everything he does in business. That mindset, paired with his reputation as a thoughtful connector, has earned him trust from agency leaders across the states. And with systems like Relationship Digest, he’s found a way to scale those relationships without turning them into another task on the to-do list.
In this piece, he shares how relationships have opened doors, stayed alive through systems, and matured into one of the most fulfilling parts of his career.
Just Trust, Built Over Time..
Leonard Chin: What’s an instance when a relationship led to a big win or a really great opportunity for your business?
Steve Guberman:
“Relationships are the foundation of everything I do in business. I don’t believe I can effectively work with a client who doesn’t know, like, and trust me—and that trust only comes from investing in the relationship first. Similarly, clients don’t stick around long-term unless they feel genuinely valued and prioritized as people, not just accounts.
When I first launched Agency Outsight, I spent weeks talking with about a dozen agency owner friends each week. These weren’t sales calls—they were curiosity calls. I wanted to deeply understand what was really happening in the agency world and what challenges founders were facing inside their businesses.
Within the same week, three different agency founders—people I’d known for over a decade—independently told me I had to connect with the same person: a former agency founder who had successfully exited and was now coaching agency owners. I reached out, we connected, and over time we built a genuine relationship—not just as peers in business, but as friends who supported each other through both professional shifts and personal life moments.
As they gradually stepped back from agency coaching, they began passing inbound leads my way. They also recommended me as a speaker to an agency event they had spoken at for several years. Based purely on their recommendation, the event organizer reached out and invited me to speak—no vetting, no audition, no hesitation.
That single speaking engagement led to two new clients within a few months. All of it traced back to relationships I had invested in for over a decade. No funnel. No pitch. Just trust, built over time.”
CRM Activities with Prompts..
Leonard Chin: What's your daily/weekly routine for maintaining relationships that help your business?
Steve Guberman:
“I intentionally block time on my calendar for what I call “CRM activities.” This is dedicated space to look at stalled conversations, past connections, and relationships that I haven’t nurtured recently—but should.
Historically, that meant digging through my inbox or CRM and hoping I didn’t miss someone important. Tools like Relationship Digest have been absolute rocket fuel here. Having thoughtful, automated prompts surface people I should reconnect with saves me from relying on memory alone—which, let’s be honest, gets unreliable when you’re busy.
What I love most is that it doesn’t overwhelm me. I get just enough prompts to take meaningful action without derailing my time block or turning relationship-building into another stressful task. It keeps the human part of my business human—while still being consistent.”
Earlier, More Systematic Nurturing..
Leonard Chin: What tips would you give to your younger self around relationships and how they impact business?
Steve Guberman:
“Early in my career, I was taught that “your network is your net worth,” and while I believed it, I didn’t always act on it consistently. I focused heavily on business development and execution, but I didn’t invest enough time in relationship nurturing—for support, for friendship, or simply for staying connected as people evolved.
One of my love languages is connecting people. I genuinely thrive on introducing people where something meaningful comes from it—new careers, businesses, long-term friendships, even romantic relationships. Watching those connections grow over years is incredibly fulfilling to me.
If I could go back, I’d tell my younger self to build a more intentional, routine, and systematic approach to nurturing relationships much earlier. Not in a transactional way—but in a way that honors the fact that relationships are living things. They need care, attention, and presence. The sooner I learned that, the more impact—and fulfillment—I would have created earlier on.”
Key Takeaways.
We’re glad to have Steve Guberman with us on this week’s series, and here are the few key takeaways:
Long-term trust wins. A single relationship led to a speaking gig and new clients without pitching or hesitation. Just years of genuine connection.
Low-friction tools help. Steve uses Relationship Digest to surface prompts and keep outreach human, not stressful.
Be systematic early. He’d tell his younger self to treat relationships like living things… routine, intentional care pays off.
That’s all for now.
If you're open to sharing your experiences in one of our future articles… or know of someone who is, feel free to drop me an email here.
Author.
Leonard Chin
Follow me on LinkedIn.
Steve Guberman.
This week, we’re spotlighting Steve Guberman, an agency growth coach and M&A advisor at Agency Outsight, a relationship-first advisory firm that helps founders scale, strengthen, and prepare their agencies for acquisition. He’s also the host of Agency Bytes, the go-to podcast for agency owners.
But Steve isn’t just another coach cheering from the sidelines.
Before launching Outsight, he founded Fifth Room Creative… a boutique agency named after the fifth room of his own home, where he felt the most creative. That firsthand experience as a founder shapes everything he does today. He’s not guessing the pressures agency owners face. He’s lived them.
What truly sets Steve apart isn’t just his frameworks.
It’s his philosophy.
He believes relationships are the foundation of everything he does in business. That mindset, paired with his reputation as a thoughtful connector, has earned him trust from agency leaders across the states. And with systems like Relationship Digest, he’s found a way to scale those relationships without turning them into another task on the to-do list.
In this piece, he shares how relationships have opened doors, stayed alive through systems, and matured into one of the most fulfilling parts of his career.
Just Trust, Built Over Time..
Leonard Chin: What’s an instance when a relationship led to a big win or a really great opportunity for your business?
Steve Guberman:
“Relationships are the foundation of everything I do in business. I don’t believe I can effectively work with a client who doesn’t know, like, and trust me—and that trust only comes from investing in the relationship first. Similarly, clients don’t stick around long-term unless they feel genuinely valued and prioritized as people, not just accounts.
When I first launched Agency Outsight, I spent weeks talking with about a dozen agency owner friends each week. These weren’t sales calls—they were curiosity calls. I wanted to deeply understand what was really happening in the agency world and what challenges founders were facing inside their businesses.
Within the same week, three different agency founders—people I’d known for over a decade—independently told me I had to connect with the same person: a former agency founder who had successfully exited and was now coaching agency owners. I reached out, we connected, and over time we built a genuine relationship—not just as peers in business, but as friends who supported each other through both professional shifts and personal life moments.
As they gradually stepped back from agency coaching, they began passing inbound leads my way. They also recommended me as a speaker to an agency event they had spoken at for several years. Based purely on their recommendation, the event organizer reached out and invited me to speak—no vetting, no audition, no hesitation.
That single speaking engagement led to two new clients within a few months. All of it traced back to relationships I had invested in for over a decade. No funnel. No pitch. Just trust, built over time.”
CRM Activities with Prompts..
Leonard Chin: What's your daily/weekly routine for maintaining relationships that help your business?
Steve Guberman:
“I intentionally block time on my calendar for what I call “CRM activities.” This is dedicated space to look at stalled conversations, past connections, and relationships that I haven’t nurtured recently—but should.
Historically, that meant digging through my inbox or CRM and hoping I didn’t miss someone important. Tools like Relationship Digest have been absolute rocket fuel here. Having thoughtful, automated prompts surface people I should reconnect with saves me from relying on memory alone—which, let’s be honest, gets unreliable when you’re busy.
What I love most is that it doesn’t overwhelm me. I get just enough prompts to take meaningful action without derailing my time block or turning relationship-building into another stressful task. It keeps the human part of my business human—while still being consistent.”
Earlier, More Systematic Nurturing..
Leonard Chin: What tips would you give to your younger self around relationships and how they impact business?
Steve Guberman:
“Early in my career, I was taught that “your network is your net worth,” and while I believed it, I didn’t always act on it consistently. I focused heavily on business development and execution, but I didn’t invest enough time in relationship nurturing—for support, for friendship, or simply for staying connected as people evolved.
One of my love languages is connecting people. I genuinely thrive on introducing people where something meaningful comes from it—new careers, businesses, long-term friendships, even romantic relationships. Watching those connections grow over years is incredibly fulfilling to me.
If I could go back, I’d tell my younger self to build a more intentional, routine, and systematic approach to nurturing relationships much earlier. Not in a transactional way—but in a way that honors the fact that relationships are living things. They need care, attention, and presence. The sooner I learned that, the more impact—and fulfillment—I would have created earlier on.”
Key Takeaways.
We’re glad to have Steve Guberman with us on this week’s series, and here are the few key takeaways:
Long-term trust wins. A single relationship led to a speaking gig and new clients without pitching or hesitation. Just years of genuine connection.
Low-friction tools help. Steve uses Relationship Digest to surface prompts and keep outreach human, not stressful.
Be systematic early. He’d tell his younger self to treat relationships like living things… routine, intentional care pays off.
That’s all for now.
If you're open to sharing your experiences in one of our future articles… or know of someone who is, feel free to drop me an email here.
Author.
Leonard Chin
Follow me on LinkedIn.