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What if the best way to stand out in an inbox full of AI is to show up as a human? Gus sits down with Abe Dearmer, CEO of Sendspark, an AI video platform owned by Xenon Partners, calling in at 5 AM from Australia.
Abe grew up playing rugby union, went into the Australian Army straight out of school, and was told on his aptitude test that he should be an officer instead of an infantry rifleman. Thirteen years later, Xenon offered him a way out. Since then he has worked at integrate.io and led the acquisitions of 5CRM and Teamgate, including steering 5CRM toward addiction recovery providers after they wrote about the product without being asked. Today he runs Sendspark with one North Star: how do we help salespeople close more deals?
Abe describes his own AI aha moment: building a powerlifting app, Iron Ledger, over a weekend and getting it onto the App Store. He talks about the "AI psychosis" that follows, why the owner has to go first, how his team keeps a human in the loop on everything that ships, and what happened when the whole Xenon portfolio paused for a week-long AI hackathon. Then he walks Gus through a live Sendspark demo, plus the automated outbound agent he built himself.
What we get into:
Rugby, the Army and building a team environment
Clear, measurable goals as a way to find people's strengths
Finding an unexpected market: 5CRM and addiction recovery
Building human connection through video before the first demo
"Be a red X in a room full of white circles"
Don't tell me, show me: using video to drive adoption
Building Iron Ledger over a weekend, and the beekeeper who built his own app
AI psychosis, session limits and feature sprawl
Why the owner has to go first: start with a problem, get a subscription, just talk to it
Human in the loop: AI never pushes to staging or production
"What did I do in AI this week?" and the portfolio-wide hackathon
Live demo: dynamic videos, AI greetings and personalized landing pages
An outbound agent that runs every week without him touching it
Timestamps
00:00 Meet Abe Dearmer
00:59 Rugby union and the love of team
03:11 Light and shadow: amplifying what works on a team
05:51 The Army, the aptitude test and becoming an officer
08:08 From the military to Xenon
08:46 integrate.io, 5CRM and Teamgate
11:55 What Sendspark does
15:02 Video as trust before the first call
19:21 Using Sendspark to drive client engagement
23:22 People's favorite word is their first name
24:28 Abe's AI aha moment: Iron Ledger
29:14 When the AI clone beats the source video
30:52 Analog, digital, agentic: does the owner have to go first?
36:15 AI psychosis and feature sprawl
41:32 Resistance, safety and the $500K API bill
43:38 Human in the loop on every release
45:32 "What did I do in AI this week?" and the hackathon
48:44 People are naturally creative
50:39 Live Sendspark demo
60:17 A/B testing video vs. no video
61:41 Abe's automated outbound agent
65:34 Remember, forget, succeed, fail: implementation and mastery
About the guest
Abe Dearmer is the CEO of Sendspark, an AI video platform owned by Xenon Partners. A 13-year Australian Army veteran, he has led software companies through acquisition, stabilization and handoff across the Xenon portfolio, including integrate.io, 5CRM and Teamgate.
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
What happens when everyone in your company is already using AI and nobody has written down the rules? I sit down with Richard Schreiber, who has been in legal operations since 1983 and spent 25 years leading major technology overhauls for law firms. Today he helps leaders use AI safely and ethically without losing what makes their work human.
Richard founded Law Firm AI Expert and Secure Justice AI. He is the author of four books, a journalist, co-host of the weekly True Journalism podcast, and a longtime autism advocate whose work was inspired by his daughter. We are both New Yorkers and both parents of kids on the spectrum.
He lays out the AI governance landscape: no federal AI law, a patchwork of state laws, more than 1,400 court cases with AI hallucinations in the last year alone, and why AI is not like software. He explains why governance has to come before rollout, why "people confuse speed with accuracy," and why quantum computing makes harvested data a risk today. Then we talk about young people's resistance to AI, AI stewardship, AI for good in the autism community, and the first thing any firm should do this month.
What we get into:
Why AI is moving faster than its guardrails
No federal AI law and a quilt of state rules
Open-source models, containerized
AI hygiene and the epidemic of hallucinations in court
The gap between employees using AI and firms with SOPs and training
Agents that escape their sandbox, and why governance comes first
Quantum computing and "harvest now, decrypt later"
Chat, skills, co-work: the move to digital employees
Speed is not accuracy: models designed to hallucinate
Young creatives, AI stewardship and protecting your IP
AI for good: early detection, early intervention and connection for neurodivergent kids
Start with a governance plan
Timestamps
00:00 Meet Richard Schreiber
01:01 The AI landscape: speed without guardrails
03:46 No federal AI law, a patchwork of states
06:56 Open-source models and the cost differential
08:28 Lessons from cybersecurity
10:14 AI is not like software: hallucinations in court
11:44 Everyone uses AI, few firms have SOPs
15:32 When agents escape their sandbox
16:32 Law Firm AI Expert and Secure Justice AI
18:19 Quantum computing explained
21:51 Precision wellness and autism research
22:53 Chat, skills, co-work: digital employees
26:21 Bridging utilization and implementation
28:49 Think AI first, keep a human in the loop
31:45 People confuse speed with accuracy
32:49 Hallucinations at the highest levels and the case for governance
35:14 Social media, our kids and accountability
35:45 Young people booing AI
36:49 AI stewardship for creatives
40:00 Integrate to elevate
41:21 AI for good in the autism community
45:29 The first thing to do: start with governance
48:22 AI is a genius intern
49:51 Where to find Richard
About the guest
Richard Schreiber has worked in legal operations since 1983 and spent 25 years leading technology overhauls for law firms. He is the founder of Law Firm AI Expert and Secure Justice AI, the author of four books, a journalist, co-host of the True Journalism podcast, writes the Legal AI Strategist Substack, and is a longtime autism advocate. LinkedIn is a great way to connect with him.
Law Firm AI Expert:
https://lawfirmaiexpert.com
Secure Justice AI:
https://securejusticeai.com
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
What if the skills that help you understand an autistic child are the same ones that close more deals? Megan Killion and I share a lot. We both grew up on Cape Cod, in Dennis, and Megan, like my son, grew up with autism and sensory processing challenges.
Megan got pregnant her senior year of high school and had her first six-figure year at 19 as a single mom. Before that she was homeless, baiting tackle through a Cape Cod winter to feed her kid. Sales changed her life. She ran sales and marketing for StreamGuys and CacheFly, led business development at Ericsson, built an agency to help people without the same opportunities get into sales and marketing, and has helped build more than $550 million in client pipeline. Then came an ovarian cancer diagnosis. She sold the agency and rebuilt her life around one idea: do less, better.
She gives parents practical, compassionate advice on meeting autistic kids where they are, then shows how the same principle, getting into the world of the person in front of you, is the foundation of great discovery, great sales and great relationships.
What we get into:
Timestamps
About the guest
Megan Killion is a revenue architect for MSPs and founder led B2B technology companies, chief consultant at Pisces Growth, and the author of The MSP Sales Playbook, available on Amazon. LinkedIn is the best way to connect with her.
LinkedIn: https://www.linkedin.com/in/megankillion
Website: https://megankillion.com
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
It took most businesses 10 or 12 years to get on board when we moved from analog to digital. The move from digital to agentic? Gus thinks you might have 12 months.
In this one Gus walks me back through the three eras I have lived in business: analog, digital and now agentic. In the analog days I was the consultant who carried the answers, left behind a binder and a plan, and hoped. I was spending about 20 percent of my time doing what I loved and 80 percent on everything else. Digital changed the tools, but it did not change the inside. I was still trying to be controlling instead of putting controls in place.
Then I almost got killed on a bike, walked home with two broken ribs, and my wife asked me, "Are you done?" I said yes, sold the business, and tried retirement: beekeeping, gardening, pickleball, golf. It did not take. What brought me back was meeting Gus and seeing an AI SDR fill a calendar while he slept. I don't believe in retirement. I believe in rewiring.
What we get into:
Timestamps
About the guest
Gus Waite is the founder of Independent Brokers Collective and my co-host on DelegAIte. Former NYC managing broker, former actor and stand up comedian, current Cape Cod resident who will absolutely make you laugh before he makes you think.
IB Collective: https://ibcollective.ai
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
What if you did everything right in your career and still did not feel financially free? That is where Dr. Matt Markel found himself.
Matt went from entry level engineer to the C-suite: head of radar at Waymo, CEO of Spartan Radar, CTO at Epirus, with patents in radar and defense technology. He grew up with a heavy scarcity mindset, and after decades of doing everything the playbook said, he still did not feel free. So he built Strata, which teaches eight habits for financial independence grouped into three areas: capture money before lifestyle spends it, govern it in a smart way, and protect it.
We talk about why success and wealth are two different games, how our generation got moved from defined benefit to defined contribution and quietly took on all the risk, why ownership beats effort, and his book, Anti-preneur, which makes the case that you can build wealth without quitting the career you worked so hard for. And the line I keep coming back to: you cannot consistently behave in a manner that is inconsistent with how you see yourself.
What we get into:
Timestamps
About the guest
Dr. Matt Markel is the founder of Strata Financial Education and the author of Anti-preneur. Former head of radar at Waymo, CEO of Spartan Radar and CTO at Epirus. This episode is for informational purposes only and is not financial advice.
Strata: https://learnstrata.com
LinkedIn: https://www.linkedin.com/in/matt-markel
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
Most conversations about delegation start with mechanics: what to hand over, to whom, and in what order. My guest today says that is the second question. The first one is harder. What actually belongs on your plate in the first place?
Remy Meraz is the co-founder and president of Zella Life, a coaching and behavioral analytics platform that received funding from Google's Latino Founders Fund. She started doing the inner work because of a toxic boss whose leadership by fear and intimidation made her and four other people sick. Later she left her marriage, went from a six-figure salary to nothing, moved into a studio, watched her first venture go down, and got fired from the job she took to get by. Once she started building Zella, the first corporate client and the Google funding followed within a couple of months.
We get into why strong individual contributors struggle when they become managers, why delegation is an inside job, psychological safety and the cost of silence, and how AI can reduce cognitive load without replacing empathy and human connection. Her one piece of advice: build yourself first.
What we get into:
Timestamps
About the guest
Remy Meraz is the co-founder and president of Zella Life, a coaching and behavioral analytics platform. She offers a complimentary coaching session through the Zella Life website.
Zella Life: https://zellalife.com
LinkedIn: https://www.linkedin.com/in/remy-meraz/
Email: [email protected]
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
Most people in logistics will tell you the problem is speed. Quote faster, book faster, move faster. My guest today thinks that is the wrong diagnosis. Going faster without better judgment just moves the mistake further down the line.
Chris Condon started out driving a forklift in a container yard in Kent, Washington in 1995. He spent 16 years at Expeditors, took over a freight company that was $59 million in debt and had it profitable inside one year, then built and sold another one. Today he runs Aircon, an AI platform for air freight forwarders.
The reason I wanted him on: he walked away from a part of the business that was making money because it was not the company he needed to exist. Running a tech enabled wholesaler alongside a tech brand confused the market and put his neutrality in question, so he cut it. What he found next is that most of his customers are missing 30 to 40 percent of their inputs, and the quote is just the visible output of the work.
What we get into:
Timestamps
About the guest
Chris Condon is the founder of Aircon, an AI platform for air freight forwarders. He started on a forklift in Kent, Washington, spent 16 years at Expeditors, and turned around a freight company carrying $59 million in debt. He welcomes engagement from the industry on LinkedIn.
Aircon: https://aircon.ai
LinkedIn: https://www.linkedin.com/in/chris-condon-air-freight-ai/
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
My guest today lost his brother to a misdiagnosis. His brother was a cardiologist. Think about that for a second: a physician inside the system, with every advantage, and the system still missed it.
Dr. Steven Charlap is a surgeon trained at NYU with an MBA from Harvard. He spent 21 years co-founding and running HealthDrive, a mobile medical company that served over five million patients across 13 states, made the Inc. 500 twice and exited to private equity. He gave his personal phone number to the families of his patients. He could have stopped there. Instead he spent the last decade, and over four million dollars of his own money, building MEDOME.ai, an AI powered personal health record that runs the full medical interview, applies more than 500 algorithms, and hands you back the questions your doctor does not have time to ask.
His answer to what his brother's story teaches us is three words: trust but verify. Doctors are human, under pressure, and there are 28,000 diseases. When he first went to doctors with MEDOME, some told him they did not want more information on their patients. So he built it for the rest of us.
What we get into:
Timestamps
About the guest
Dr. Steven Charlap is a surgeon trained at NYU, a Harvard MBA, and the co-founder of HealthDrive, which served over five million patients across 13 states. He is the founder of MEDOME.ai, an AI powered personal health record. This episode is for informational purposes only and is not medical advice.
MEDOME: https://medome.ai
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
Every founder I know has had the same instinct at least once. Growth stalls, so we lean in. Work harder, do more. More meetings, more approvals, more of you. My guest today did exactly that and watched it make things worse.
Vlad Podoliako started out as a researcher finding sales leads in Kyiv. Two years later he was chief data officer. In 2017 he founded Belkins, now one of the highest rated B2B client acquisition firms in the world, and built it without outside money. He is a Forbes 30 Under 30, and today he has 16 companies. When Belkins hit the wall, what finally worked was Vlad stepping back from an entire function and letting someone else genuinely own it. Results improved because he was not there.
We get into the 80% rule, the need to be needed, the hostage relationship between owners and indispensable employees, and why memory, a company brain built from your own knowledge, is the foundation of an AI native company.
What we get into:
Timestamps
About the guest
Vlad Podoliako is the founder of Belkins, a B2B client acquisition firm he built without outside money, and a Forbes 30 Under 30. He started as a researcher finding sales leads in Kyiv and was chief data officer two years later. LinkedIn is the best place to find him.
LinkedIn: https://www.linkedin.com/in/chiefdata
Belkins: https://belkins.io/contact-us
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
Eight years. Tens of millions of dollars. Not one unit sold. That is what it took Cody Simmons and his team to get DermaSensor through the FDA, the first automated skin cancer detection device cleared for primary care doctors. And the first three people on the team are still working together nine years later.
Cody is the co-founder and CEO of DermaSensor. Time named it one of the best inventions of 2024, and it landed on Inc's list alongside Anthropic and NVIDIA. He did his graduate work in bioengineering at Stanford and spent four years at Genentech before joining his co-founder, a serial medical device entrepreneur, to turn a research technology into a company.
Skin cancer is the cancer you can see, and yet only about eight percent of the hundred million Americans at risk get the recommended annual skin exam. I know why people avoid it. I sat on a mole for a long time because I did not want to hear the answer. So we walked through the four things every founder building something hard runs into: regulation, capital, trust and scale. And Cody told me about the second patient ever scanned after clearance, a man who was sure his mole was fine. It came back a 10 out of 10.
What we get into:
Timestamps
About the guest
Cody Simmons is the co-founder and CEO of DermaSensor, the first automated skin cancer detection device cleared by the FDA for primary care doctors. Stanford bioengineering, four years at Genentech, and ten years into building DermaSensor. He is responsive on LinkedIn.
DermaSensor: https://www.dermasensor.com/
LinkedIn: https://www.linkedin.com/in/codyvsimmons/
Want to be a guest? We are looking for real operators, not celebrities. Fill out the guest form at the link below:
https://forms.gle/guCp7wDBoUjkX86t7
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