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Mar 12, 2024 · 35m · we-live-to-build

He Told His Son 'Watch What Happens When You Turn 35

Glenn Akramoff · 17m spoken Sean Weisbrot · 14m spoken
0:00 / 0:00
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this podcast episode, host Sean Weisbrot and consultant Glenn Akramoff explore the complexities of operating family-owned businesses, focusing on father-son workplace dynamics, overcoming generational resistance, and executing digital transformation. Drawing from their personal and consulting experiences, they offer practical insights into establishing healthy emotional boundaries, modernizing legacy workflows, and planning for business succession.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 43.5% of the talking time here. How this is scored →

Sean as informed peer 4.8 Guest teaching 1.6 Guest disagreement 0.4 Sean pushing back 0.1
05100:0010:0020:0030:000:00–2:11 · Sean as informed peer 5/10 The Magic Age of 35 in Business Sean introduces the podcast and shares his own past experience running his father's practice while Glenn offers an observation about society's bias against professionals under 35.2:11–4:50 · Sean as informed peer 4/10 Navigating the Father-Son Work Dynamic Sean asks how Glenn navigates the dual roles of boss and father. Glenn explains using third-party feedback and separating family time from business discussions.4:50–7:43 · Sean as informed peer 6/10 Sean's Experience Managing His Father's Dental Practice Sean shares an extended monologue detailing how he stepped into his father's dental practice to restructure operations and replace resistant staff.7:43–10:18 · Sean as informed peer 4/10 Son's Role in Scaling and Establishing Trust Glenn explains his son's role in scaling founder-led businesses and how establishing internal trust mitigates external pushback from vendors.10:19–12:48 · Sean as informed peer 6/10 Workplace Resistance to Modernization and Age Biases Sean relates how tenured staff resented technological changes, and Glenn validates the insight by noting how workers stubbornly defend inefficient workarounds.12:48–16:24 · Sean as informed peer 7/10 Modernizing Inefficient Systems: Electronic Insurance Claims Sean illustrates a concrete case study of eliminating paper claims to reduce accounts receivable from $80,000 to $20,000, which Glenn affirms as major operational value.16:24–18:57 · Sean as informed peer 4/10 Digital Transformation and Overcoming Operational Resistance Glenn describes the friction and ultimate benefit when his son transitioned company files from thumb drives to Google Drive, leading to staffing adjustments.18:57–24:20 · Sean as informed peer 4/10 Mid-Roll Intermission: Host Channel Subscription Call Following a mid-roll channel plug, Sean and Glenn explore how cloud platforms and project management tools like Asana streamlined client workflows.24:20–27:30 · Sean as informed peer 7/10 Automating Business Workflows with Zapier Integrations Sean demonstrates deep technical expertise by describing how he configured Zapier to automate end-to-end CRM and scheduling funnels without assistants.27:30–30:03 · Sean as informed peer 4/10 Succession Planning and Preserving the Family Legacy Glenn reflects on succession planning, leaving open options for his son to take over the firm while maintaining honor for the family name.30:03–32:32 · Sean as informed peer 3/10 Greatest Lessons and Hardest Challenges in Family Business Glenn recounts the most challenging episode of working with his son, including accidentally sending a text about firing him directly to the son.32:32–35:25 · Sean as informed peer 5/10 Unspoken Bonds and Discovering Parental Vulnerabilities Sean and Glenn bond over the unique perspective gained from working with fathers, noting both the strengths and business vulnerabilities that become visible.35:25–35:52 · Sean as informed peer 3/10 The Lifelong Value of Learning from Anyone Glenn shares a final piece of wisdom inherited from his father about remaining open to learning from anyone, ending the interview on a collaborative note.0:00–2:11 · Guest teaching 3/10 The Magic Age of 35 in Business Sean introduces the podcast and shares his own past experience running his father's practice while Glenn offers an observation about society's bias against professionals under 35.2:11–4:50 · Guest teaching 2/10 Navigating the Father-Son Work Dynamic Sean asks how Glenn navigates the dual roles of boss and father. Glenn explains using third-party feedback and separating family time from business discussions.4:50–7:43 · Guest teaching 0/10 Sean's Experience Managing His Father's Dental Practice Sean shares an extended monologue detailing how he stepped into his father's dental practice to restructure operations and replace resistant staff.7:43–10:18 · Guest teaching 2/10 Son's Role in Scaling and Establishing Trust Glenn explains his son's role in scaling founder-led businesses and how establishing internal trust mitigates external pushback from vendors.10:19–12:48 · Guest teaching 2/10 Workplace Resistance to Modernization and Age Biases Sean relates how tenured staff resented technological changes, and Glenn validates the insight by noting how workers stubbornly defend inefficient workarounds.12:48–16:24 · Guest teaching 1/10 Modernizing Inefficient Systems: Electronic Insurance Claims Sean illustrates a concrete case study of eliminating paper claims to reduce accounts receivable from $80,000 to $20,000, which Glenn affirms as major operational value.16:24–18:57 · Guest teaching 2/10 Digital Transformation and Overcoming Operational Resistance Glenn describes the friction and ultimate benefit when his son transitioned company files from thumb drives to Google Drive, leading to staffing adjustments.18:57–24:20 · Guest teaching 1/10 Mid-Roll Intermission: Host Channel Subscription Call Following a mid-roll channel plug, Sean and Glenn explore how cloud platforms and project management tools like Asana streamlined client workflows.24:20–27:30 · Guest teaching 1/10 Automating Business Workflows with Zapier Integrations Sean demonstrates deep technical expertise by describing how he configured Zapier to automate end-to-end CRM and scheduling funnels without assistants.27:30–30:03 · Guest teaching 2/10 Succession Planning and Preserving the Family Legacy Glenn reflects on succession planning, leaving open options for his son to take over the firm while maintaining honor for the family name.30:03–32:32 · Guest teaching 2/10 Greatest Lessons and Hardest Challenges in Family Business Glenn recounts the most challenging episode of working with his son, including accidentally sending a text about firing him directly to the son.32:32–35:25 · Guest teaching 1/10 Unspoken Bonds and Discovering Parental Vulnerabilities Sean and Glenn bond over the unique perspective gained from working with fathers, noting both the strengths and business vulnerabilities that become visible.35:25–35:52 · Guest teaching 2/10 The Lifelong Value of Learning from Anyone Glenn shares a final piece of wisdom inherited from his father about remaining open to learning from anyone, ending the interview on a collaborative note.0:00–2:11 · Guest disagreement 1/10 The Magic Age of 35 in Business Sean introduces the podcast and shares his own past experience running his father's practice while Glenn offers an observation about society's bias against professionals under 35.2:11–4:50 · Guest disagreement 1/10 Navigating the Father-Son Work Dynamic Sean asks how Glenn navigates the dual roles of boss and father. Glenn explains using third-party feedback and separating family time from business discussions.4:50–7:43 · Guest disagreement 0/10 Sean's Experience Managing His Father's Dental Practice Sean shares an extended monologue detailing how he stepped into his father's dental practice to restructure operations and replace resistant staff.7:43–10:18 · Guest disagreement 1/10 Son's Role in Scaling and Establishing Trust Glenn explains his son's role in scaling founder-led businesses and how establishing internal trust mitigates external pushback from vendors.10:19–12:48 · Guest disagreement 1/10 Workplace Resistance to Modernization and Age Biases Sean relates how tenured staff resented technological changes, and Glenn validates the insight by noting how workers stubbornly defend inefficient workarounds.12:48–16:24 · Guest disagreement 0/10 Modernizing Inefficient Systems: Electronic Insurance Claims Sean illustrates a concrete case study of eliminating paper claims to reduce accounts receivable from $80,000 to $20,000, which Glenn affirms as major operational value.16:24–18:57 · Guest disagreement 0/10 Digital Transformation and Overcoming Operational Resistance Glenn describes the friction and ultimate benefit when his son transitioned company files from thumb drives to Google Drive, leading to staffing adjustments.18:57–24:20 · Guest disagreement 0/10 Mid-Roll Intermission: Host Channel Subscription Call Following a mid-roll channel plug, Sean and Glenn explore how cloud platforms and project management tools like Asana streamlined client workflows.24:20–27:30 · Guest disagreement 0/10 Automating Business Workflows with Zapier Integrations Sean demonstrates deep technical expertise by describing how he configured Zapier to automate end-to-end CRM and scheduling funnels without assistants.27:30–30:03 · Guest disagreement 0/10 Succession Planning and Preserving the Family Legacy Glenn reflects on succession planning, leaving open options for his son to take over the firm while maintaining honor for the family name.30:03–32:32 · Guest disagreement 1/10 Greatest Lessons and Hardest Challenges in Family Business Glenn recounts the most challenging episode of working with his son, including accidentally sending a text about firing him directly to the son.32:32–35:25 · Guest disagreement 0/10 Unspoken Bonds and Discovering Parental Vulnerabilities Sean and Glenn bond over the unique perspective gained from working with fathers, noting both the strengths and business vulnerabilities that become visible.35:25–35:52 · Guest disagreement 0/10 The Lifelong Value of Learning from Anyone Glenn shares a final piece of wisdom inherited from his father about remaining open to learning from anyone, ending the interview on a collaborative note.0:00–2:11 · Sean pushing back 0/10 The Magic Age of 35 in Business Sean introduces the podcast and shares his own past experience running his father's practice while Glenn offers an observation about society's bias against professionals under 35.2:11–4:50 · Sean pushing back 1/10 Navigating the Father-Son Work Dynamic Sean asks how Glenn navigates the dual roles of boss and father. Glenn explains using third-party feedback and separating family time from business discussions.4:50–7:43 · Sean pushing back 0/10 Sean's Experience Managing His Father's Dental Practice Sean shares an extended monologue detailing how he stepped into his father's dental practice to restructure operations and replace resistant staff.7:43–10:18 · Sean pushing back 0/10 Son's Role in Scaling and Establishing Trust Glenn explains his son's role in scaling founder-led businesses and how establishing internal trust mitigates external pushback from vendors.10:19–12:48 · Sean pushing back 0/10 Workplace Resistance to Modernization and Age Biases Sean relates how tenured staff resented technological changes, and Glenn validates the insight by noting how workers stubbornly defend inefficient workarounds.12:48–16:24 · Sean pushing back 0/10 Modernizing Inefficient Systems: Electronic Insurance Claims Sean illustrates a concrete case study of eliminating paper claims to reduce accounts receivable from $80,000 to $20,000, which Glenn affirms as major operational value.16:24–18:57 · Sean pushing back 0/10 Digital Transformation and Overcoming Operational Resistance Glenn describes the friction and ultimate benefit when his son transitioned company files from thumb drives to Google Drive, leading to staffing adjustments.18:57–24:20 · Sean pushing back 0/10 Mid-Roll Intermission: Host Channel Subscription Call Following a mid-roll channel plug, Sean and Glenn explore how cloud platforms and project management tools like Asana streamlined client workflows.24:20–27:30 · Sean pushing back 0/10 Automating Business Workflows with Zapier Integrations Sean demonstrates deep technical expertise by describing how he configured Zapier to automate end-to-end CRM and scheduling funnels without assistants.27:30–30:03 · Sean pushing back 0/10 Succession Planning and Preserving the Family Legacy Glenn reflects on succession planning, leaving open options for his son to take over the firm while maintaining honor for the family name.30:03–32:32 · Sean pushing back 0/10 Greatest Lessons and Hardest Challenges in Family Business Glenn recounts the most challenging episode of working with his son, including accidentally sending a text about firing him directly to the son.32:32–35:25 · Sean pushing back 0/10 Unspoken Bonds and Discovering Parental Vulnerabilities Sean and Glenn bond over the unique perspective gained from working with fathers, noting both the strengths and business vulnerabilities that become visible.35:25–35:52 · Sean pushing back 0/10 The Lifelong Value of Learning from Anyone Glenn shares a final piece of wisdom inherited from his father about remaining open to learning from anyone, ending the interview on a collaborative note.

speaking balance: gold is Sean, purple is the guest (3 minute bins)

0:00 · Sean 66.9% · guest 33.1%0:00 · Sean 66.9% · guest 33.1%3:00 · Sean 38.6% · guest 61.4%3:00 · Sean 38.6% · guest 61.4%6:00 · Sean 63.9% · guest 36.1%6:00 · Sean 63.9% · guest 36.1%9:00 · Sean 40.9% · guest 59.1%9:00 · Sean 40.9% · guest 59.1%12:00 · Sean 68.4% · guest 31.6%12:00 · Sean 68.4% · guest 31.6%15:00 · Sean 40.2% · guest 59.8%15:00 · Sean 40.2% · guest 59.8%18:00 · Sean 41% · guest 59%18:00 · Sean 41% · guest 59%21:00 · Sean 13.9% · guest 86.1%21:00 · Sean 13.9% · guest 86.1%24:00 · Sean 70.6% · guest 29.4%24:00 · Sean 70.6% · guest 29.4%27:00 · Sean 20.4% · guest 79.6%27:00 · Sean 20.4% · guest 79.6%30:00 · Sean 8% · guest 92%30:00 · Sean 8% · guest 92%33:00 · Sean 50.1% · guest 49.9%33:00 · Sean 50.1% · guest 49.9%
Sharpest disagreement ▶ 31:08 Accidental firing text revelation

Glenn reveals the heightened emotional tension of family business disputes, admitting he mistakenly sent an 'I want to fire him' text directly to his son.

 Hardest push from Sean ▶ 22:47 Software preference pushback

Sean gently pushes back on Glenn's choice of Asana by asserting his own preference for ClickUp before allowing Glenn to explain his team's rationale.

 Biggest teaching moment ▶ 11:50 Psychology of workplace workarounds

Glenn educates Sean on organizational change management, breaking down how employees cling defensively to broken workarounds even when faster modern solutions exist.

 Sean holds their own ▶ 24:35 Sean's Zapier automation blueprint

Sean demonstrates strong operational mastery by laying out the exact technical pipeline he created linking web forms, Zapier, and Pipedrive to remove administrative overhead.
the scores for every segment, with the reasoning behind each
ChapterTopicSean as informed peerGuest teachingGuest disagreementSean pushing backWhy
The Magic Age of 35 in Business 5310 Sean introduces the podcast and shares his own past experience running his father's practice while Glenn offers an observation about society's bias against professionals under 35.
Navigating the Father-Son Work Dynamic 4211 Sean asks how Glenn navigates the dual roles of boss and father. Glenn explains using third-party feedback and separating family time from business discussions.
Sean's Experience Managing His Father's Dental Practice 6000 Sean shares an extended monologue detailing how he stepped into his father's dental practice to restructure operations and replace resistant staff.
Son's Role in Scaling and Establishing Trust 4210 Glenn explains his son's role in scaling founder-led businesses and how establishing internal trust mitigates external pushback from vendors.
Workplace Resistance to Modernization and Age Biases 6210 Sean relates how tenured staff resented technological changes, and Glenn validates the insight by noting how workers stubbornly defend inefficient workarounds.
Modernizing Inefficient Systems: Electronic Insurance Claims 7100 Sean illustrates a concrete case study of eliminating paper claims to reduce accounts receivable from $80,000 to $20,000, which Glenn affirms as major operational value.
Digital Transformation and Overcoming Operational Resistance 4200 Glenn describes the friction and ultimate benefit when his son transitioned company files from thumb drives to Google Drive, leading to staffing adjustments.
Mid-Roll Intermission: Host Channel Subscription Call 4100 Following a mid-roll channel plug, Sean and Glenn explore how cloud platforms and project management tools like Asana streamlined client workflows.
Automating Business Workflows with Zapier Integrations 7100 Sean demonstrates deep technical expertise by describing how he configured Zapier to automate end-to-end CRM and scheduling funnels without assistants.
Succession Planning and Preserving the Family Legacy 4200 Glenn reflects on succession planning, leaving open options for his son to take over the firm while maintaining honor for the family name.
Greatest Lessons and Hardest Challenges in Family Business 3210 Glenn recounts the most challenging episode of working with his son, including accidentally sending a text about firing him directly to the son.
Unspoken Bonds and Discovering Parental Vulnerabilities 5100 Sean and Glenn bond over the unique perspective gained from working with fathers, noting both the strengths and business vulnerabilities that become visible.
The Lifelong Value of Learning from Anyone 3200 Glenn shares a final piece of wisdom inherited from his father about remaining open to learning from anyone, ending the interview on a collaborative note.

Statements from this episode (8)

Disclosure
Akramoff bans work discussions at family gatherings to separate business and family
“We do our best to keep them separate. In that we have regular meetings that we talk about the business. And then when we're, when we have a family event, then we talk about the business maybe a little bit at the beginning, but once everybody's there, we don't …”
Glenn Akramoff Mar 12, 2024 ▶ 4:03
Insight
Akramoff: Society Refuses to Take Workers Seriously Until Age 35
“35 seems to be that magic number. You, the society says you don't know enough until you're 35 and you certainly ran into that. And that's not true. That's ridiculous. But that's what And I said, you watch when you turn 35, it'll be almost overnight. And he did…”
Glenn Akramoff Mar 12, 2024 ▶ 11:37
Insight
Akramoff: Employees Defend Inefficient Workarounds Over Faster Solutions
“That people get so tied up, they think they're clever when they find a workaround, even if it's inefficient, to a system not working right, or the update didn't run correctly, that they get so bogged down and tied to their workaround, that they defend it with …”
Glenn Akramoff Mar 12, 2024 ▶ 12:14
Assertion Not checkable as stated
Weisbrot: Electronic Claims Reduced Dental Practice Receivables From $80K to $20K
“And that single action lowered our outstanding from like 80,000 to 20,000 at any given time.”
Sean Weisbrot Mar 12, 2024 ▶ 15:02
Opinion
Akramoff: Third-Party Lead Gen Agencies Are Ineffective for Bespoke Consulting
“Lead gen and the marketing people who are going to contact us, we're not going to use. They just don't, they're not effective. They don't get our business. They don't care about our business. They care about getting money for lead gen.”
Glenn Akramoff Mar 12, 2024 ▶ 17:31
Insight
Weisbrot: Comprehensive business automation can make administrative assistants unnecessary
“You can automate a lot of different processes in your business that will save not in some instances, it doesn't just save an assistance time. It makes an assistant not necessary.”
Sean Weisbrot Mar 12, 2024 ▶ 25:42
What-if
Akramoff admits his father-son dynamic caused emotional overreactions during workplace disputes
“I also wouldn't have reacted if a regular employee did it. I wouldn't have reacted that way. I would have been very calm and very calculating about my answers and everything, but I got real emotional with him because it's, because, you know, this is my son.”
Glenn Akramoff Mar 12, 2024 ▶ 31:58
Insight
Akramoff: Working with a Parent Reveals Professional Vulnerabilities Hidden at Home
“I think it, you know, it changes the relationship because you both see each other in, in areas, in ways that you don't before. So, and that's both strengths and weakness. Cause we all have them. And when you're growing up with your dad, you don't get to see th…”
Glenn Akramoff Mar 12, 2024 ▶ 34:49
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