Stay ConnectedMeet Gabe Lullo.
Gabe Lullo is the CEO of Alleyoop, a sales development agency working with industry giants such as ZoomInfo, Salesloft, and Adobe.
He has trained over 8,000 salespeople across diverse businesses and, during his tenure in Alleyoop, he has personally hired and managed more than 1,500 SDRs.
With over two decades of experience in sales, marketing, and executive recruitment, his strategies have significantly driven Alleyoop’s growth.
"Everything we do as entrepreneurs is risk. But you can take educated guesses and educate yourself on how to do it." - Ryan Frey
Ryan started his career in the Peace Corps, building rural water systems in Bolivia, barely speaking the language and with no money to do it.
In two and a half years, he finished one project.
What he actually learned wasn't construction, it was how to find funding, design something from nothing, and grind projects out no matter how long they take.
He brought that grinder mentality into 25 years of real estate development in Missoula, Montana: infill housing, multifamily, industrial, large-scale residential, whatever deals came his way in a market of 120,000 people.
He recently entitled a 300-unit build-to-rent project and sold it rather than building it out himself, a decision he credits less to strategy and more to staying unattached to any single project and taking the right offer when it came.
Now he's focused on solving Montana's housing affordability gap with factory-built homes, 20-30% cheaper than stick-built construction, targeting the growing space between renters and first-time buyers priced out by the state's post-COVID, post-"Yellowstone effect" boom.
He's walked away from deals that looked perfect on paper over a single detail, like insufficient parking, that would have broken the project regardless of the numbers.
"Most of us, it's easy to create the vision and then just not take action. My advice: get in there and grind it out. You'll get it done."
"The day I finally stopped pretending was the day I realized I wasn't performing anymore. I was just surviving. And that wasn't something I was willing to keep calling success." - Brooke Leone Shipman, Founder of CEO Woman
Brooke was the first in her family to graduate college, raised without much structure but with a lot of drive.
As a sophomore in high school, after being screamed at on the drive to school, she looked in the mirror and decided she got to choose who she was, not her environment.
That decision carried her from straight A's to a scholarship to a climb from executive assistant to chief of staff at one of the largest fintech companies in the world.
For eight years, she was trusted with everything behind the scenes and invisible in front of it.
"So lonely, and also incredibly formative," she calls it.
Underneath the climb, she was performing a persona at work that clashed with who she actually was, telling herself she was fine for longer than she'd like to admit, because stopping meant admitting something wasn't working.
A close friend saw something in her before she saw it herself, and kept following up: what are your next steps, what do you need.
That's what cracked open a door she couldn't close.
She left her senior role with no outside capital and built CEO Woman, a personal growth platform for ambitious women, deliberately positioned as a luxury brand, not for the price point, but for the standard of women in the room.
"Redefining success never means asking less of yourself. It means getting honest about which standards are actually yours, and which ones were handed to you by someone else's agenda."
"The day I finally stopped pretending was the day I realized I wasn't performing anymore. I was just surviving. And that wasn't something I was willing to keep calling success." - Brooke Leone Shipman, Founder of CEO Woman
Brooke was the first in her family to graduate college, raised without much structure but with a lot of drive.
As a sophomore in high school, after being screamed at on the drive to school, she looked in the mirror and decided she got to choose who she was, not her environment.
That decision carried her from straight A's to a scholarship to a climb from executive assistant to chief of staff at one of the largest fintech companies in the world.
For eight years, she was trusted with everything behind the scenes and invisible in front of it.
"So lonely, and also incredibly formative," she calls it.
Underneath the climb, she was performing a persona at work that clashed with who she actually was, telling herself she was fine for longer than she'd like to admit, because stopping meant admitting something wasn't working.
A close friend saw something in her before she saw it herself, and kept following up: what are your next steps, what do you need.
That's what cracked open a door she couldn't close.
She left her senior role with no outside capital and built CEO Woman, a personal growth platform for ambitious women, deliberately positioned as a luxury brand, not for the price point, but for the standard of women in the room.
"Redefining success never means asking less of yourself. It means getting honest about which standards are actually yours, and which ones were handed to you by someone else's agenda."
“Failure was never really an option, nor was it accepted.” - Kyle Lucey
When Kyle entered financial advising in 2012, the odds were not exactly in his favor.
Roughly 89% of new advisors wash out within the first few years.
From day one, the expectation was simple: work.
Half-days, five days a week. Six to eight hours on weekends. Keep going until you built a successful practice.
And despite joining his father’s business, Kyle didn’t get an easier path.
He got a higher standard.
His father told him it would take six to eight years to develop the technical proficiency needed to truly master the business. Kyle initially took that personally.
Eventually, he realized his father was right.
That same philosophy now shapes how Kyle works with his own clients.
He doesn’t start the first meeting by talking about investments.
He starts by getting to know the person.
Are they a good fit? Can he serve them well? Can they build a relationship based on trust?
He even refuses referral business from the CPAs and attorneys he sends his clients to, a decision that once left a CPA firm asking:
“What’s the catch?”
There wasn’t one.
For Kyle, the business is ultimately about service, relationships, discipline, and doing what’s right for the client, even when there’s a short-term cost.
And his advice to anyone thinking about their financial future?
“Don’t wait.”
You don’t need millions saved to start planning. You don’t need to have everything figured out.
You just need to start making the right decisions early.
“Failure was never really an option, nor was it accepted.” - Kyle Lucey
When Kyle entered financial advising in 2012, the odds were not exactly in his favor.
Roughly 89% of new advisors wash out within the first few years.
From day one, the expectation was simple: work.
Half-days, five days a week. Six to eight hours on weekends. Keep going until you built a successful practice.
And despite joining his father’s business, Kyle didn’t get an easier path.
He got a higher standard.
His father told him it would take six to eight years to develop the technical proficiency needed to truly master the business. Kyle initially took that personally.
Eventually, he realized his father was right.
That same philosophy now shapes how Kyle works with his own clients.
He doesn’t start the first meeting by talking about investments.
He starts by getting to know the person.
Are they a good fit? Can he serve them well? Can they build a relationship based on trust?
He even refuses referral business from the CPAs and attorneys he sends his clients to, a decision that once left a CPA firm asking:
“What’s the catch?”
There wasn’t one.
For Kyle, the business is ultimately about service, relationships, discipline, and doing what’s right for the client, even when there’s a short-term cost.
And his advice to anyone thinking about their financial future?
“Don’t wait.”
You don’t need millions saved to start planning. You don’t need to have everything figured out.
You just need to start making the right decisions early.
"Every business owner takes all this advice from bigger companies to grow, but when it comes to technology, they suddenly think they know better and try to do it themselves." - David Robinson, Founder of Stratos
David’s career started as a lighting technician for concerts featuring Katy Perry, Tiesto, Jay-Z and others.
Then unexpected fatherhood pushed him into "a real job."
A family connection brought him into healthcare technology, where he helped build one of the first electronic medical record systems for reproductive endocrinology.
The catch?
He’d never done anything like it before.
So he figured it out through weeks of sleepless nights.
Then came a chance conversation at a pool bar in Palm Springs.
David approached WebMD’s former CFO and somehow knew enough about his struggling company to get his attention.
That conversation led to a job offer in New York, and eventually to working alongside the Big Four consulting firms.
That experience became the blueprint for Stratos:
Take the technology, expertise, and infrastructure that Fortune 500 companies spend millions on, and make it accessible to the mid-market businesses that are often overlooked.
David has a pretty blunt take on those businesses.
They'll follow proven advice from bigger companies when it comes to banking, sales, hiring, and structure.
Then they get to technology and think:
“This is the one area I can figure out myself.”
So they hand it to a nephew.
So they hand it to a nephew, a freelancer, someone "good with computers." A few years later, they're paying for that decision.
David’s filter for business is simple:
“If we’re not helping you make money or save money, it’s probably not a good thing to be involved in.”
His view on AI is just as pragmatic.
Vibe coding isn’t going away.
But it can’t vibe-code compliance.
Deploying an AI-built tool without a technical partner behind it is rolling the dice, and for most regulated companies, that’s a bet they can’t afford to make.
"Every business owner takes all this advice from bigger companies to grow, but when it comes to technology, they suddenly think they know better and try to do it themselves." - David Robinson, Founder of Stratos
David’s career started as a lighting technician for concerts featuring Katy Perry, Tiesto, Jay-Z and others.
Then unexpected fatherhood pushed him into "a real job."
A family connection brought him into healthcare technology, where he helped build one of the first electronic medical record systems for reproductive endocrinology.
The catch?
He’d never done anything like it before.
So he figured it out through weeks of sleepless nights.
Then came a chance conversation at a pool bar in Palm Springs.
David approached WebMD’s former CFO and somehow knew enough about his struggling company to get his attention.
That conversation led to a job offer in New York, and eventually to working alongside the Big Four consulting firms.
That experience became the blueprint for Stratos:
Take the technology, expertise, and infrastructure that Fortune 500 companies spend millions on, and make it accessible to the mid-market businesses that are often overlooked.
David has a pretty blunt take on those businesses.
They'll follow proven advice from bigger companies when it comes to banking, sales, hiring, and structure.
Then they get to technology and think:
“This is the one area I can figure out myself.”
So they hand it to a nephew.
So they hand it to a nephew, a freelancer, someone "good with computers." A few years later, they're paying for that decision.
David’s filter for business is simple:
“If we’re not helping you make money or save money, it’s probably not a good thing to be involved in.”
His view on AI is just as pragmatic.
Vibe coding isn’t going away.
But it can’t vibe-code compliance.
Deploying an AI-built tool without a technical partner behind it is rolling the dice, and for most regulated companies, that’s a bet they can’t afford to make.
"Whenever you're doing a speech or a presentation, you've got to say the lines out loud as you're doing it. If you wait till you're all done, you're going to have twice as much work." - Anne Freedman
Anne started as a journalist before becoming a speaking coach, and assumed a speech was a speech, until an early client bombed a presentation she'd written for him.
It read perfectly on the page. Out loud, from him, it was a disaster.
That's when she realized writing for the eyes and writing for the mouth aren't the same skill at all.
She founded Speak Out in 1990 and has spent thirty-five years since working with people who are wildly accomplished by every measure and still terrified to stand up and talk.
She doesn't treat that fear as a character flaw, she treats it as a skill gap: structuring the content, controlling your body and voice while delivering it, and being ready for the law of averages, because the mic will cut out or the coffee will spill eventually.
Her practice method cuts against instinct: rehearse a speech out of order, closing first, then opening, then the middle.
Only in the last few run-throughs do you go start to finish, timed.
And she's blunt about what separates people who break through from those who avoid the podium their whole career: they actually rehearse instead of trusting decades of expertise to carry them through unprepared.
"Keeping all this knowledge to yourself instead of sharing it is being selfish."
"Whenever you're doing a speech or a presentation, you've got to say the lines out loud as you're doing it. If you wait till you're all done, you're going to have twice as much work." - Anne Freedman
Anne started as a journalist before becoming a speaking coach, and assumed a speech was a speech, until an early client bombed a presentation she'd written for him.
It read perfectly on the page. Out loud, from him, it was a disaster.
That's when she realized writing for the eyes and writing for the mouth aren't the same skill at all.
She founded Speak Out in 1990 and has spent thirty-five years since working with people who are wildly accomplished by every measure and still terrified to stand up and talk.
She doesn't treat that fear as a character flaw, she treats it as a skill gap: structuring the content, controlling your body and voice while delivering it, and being ready for the law of averages, because the mic will cut out or the coffee will spill eventually.
Her practice method cuts against instinct: rehearse a speech out of order, closing first, then opening, then the middle.
Only in the last few run-throughs do you go start to finish, timed.
And she's blunt about what separates people who break through from those who avoid the podium their whole career: they actually rehearse instead of trusting decades of expertise to carry them through unprepared.
"Keeping all this knowledge to yourself instead of sharing it is being selfish."
"Stop talking about AI. Start talking about value. This is our product, this is the value we drive, and if you want to understand how we do it, we'll show you.” - Jeremy Levine
Jeremy's career didn't start in sales, it started in art school, which teaches you everything except how to make money as an artist.
He waited tables, moved to Israel, and worked call centers just to survive before finally breaking into tech.
At 41, he applied to every SDR, AE, and CSM role he could find and got exactly one callback: WalkMe.
Even that turned into a rejection email, "looking for somebody a little more junior."
He wrote back one line, signed off "forever young at heart" with a winky emoji.
Ten minutes later, he had a contract.
That decision kicked off five years at WalkMe during hypergrowth and an IPO, where he built outbound motions that landed logos like United Airlines, Walmart, and Home Depot.
He was eventually named one of Sales Hacker’s Top 50 sales professionals in the world.
Now, as CRO at an AI marketing technology company, he's blunt about the noise in his own category: every SaaS company has bolted AI onto its pitch, and almost none of them sound different because of it.
His answer isn't to out-hype the market, it's to stop competing on the buzzword and talk about what the product actually does.
He's candid that most AI messaging is aimed at investors, not customers, and confusing the two is exactly how companies end up sounding like everyone else.
"Nobody's cutting through by out-AI-ing the next guy. You cut through by going back to the product and the value."
Our TOPPODCAST Picks 
