Digital Social Hour - Episode 1379

Why Most Business Coaches Get It Wrong | Brandon Boeski
Date: May 21, 2025
Host: Sean Kelly
Guest: Brandon Boeski

Episode Overview

In this unfiltered, high-energy episode, Sean Kelly welcomes entrepreneur and business coach Brandon Boeski for his third appearance on the show. The conversation dives into the pitfalls of the modern business coaching industry, the value of authenticity and real experiences in mentorship, dating and relationship dynamics for high-achievers, and the quest for fulfillment beyond financial success. With signature candor, Brandon shares hard-won lessons from both his entrepreneurial journey and personal life, offering actionable insights for anyone navigating business, wealth, or modern relationships.

Key Discussion Points & Insights

1. The Problem with Most Business Coaches

Timestamps: 01:21, 01:44, 02:57, 25:32

• Lack of Real-World Experience:

  • Brandon emphasizes that most business coaches sell advice on things they've never actually achieved themselves.

    "Most people telling you about the stuff, they've never done the stuff. And I think it's a big problem and it leads to a lot of bad advice and a lot of people failing that could have otherwise been successful if they had good advice." (01:44, Brandon Boeski)

• Results Matter:

  • He contrasts himself with coaches who rely on recycled screenshots and outdated tactics.

    "A lot of people teach people stuff that they did once that worked one time and they show you the screenshot over and over and over, or they just tell you 'look at the thing that works' and it never actually worked in the first place." (02:57, Brandon Boeski)

• Impact over Income:

  • Brandon advocates for group sessions and communities, focusing on scale and genuine impact over the "10k–20k an hour" private coaching model.

    "If I get asked that and I have a thousand people listening or I have one person listening, it is the exact same output for me. I don't have to do any extra work, but now I can impact a thousand people instead of one." (01:23, Brandon Boeski)

2. Chasing Profit vs. Chasing Revenue

Timestamps: 03:11, 03:31

• The Myth of Never-Ending Growth:
  • Discusses the obsession with gross revenue over profit and warns most companies are not positioned for acquisition/exit.

    "A lot of people that are chasing revenue never make money because they don't understand that eventually you hit diminishing returns and it starts to actually lose you money to keep growing and growing and growing." (03:11, Brandon Boeski)

3. Personal Setbacks and Resilience

Timestamps: 04:06, 28:50, 29:01, 29:45

• Public Failure:

  • Brandon recounts losing over a million dollars on a biohacking gym during COVID, attributing it to a lack of focus and bad timing:

    "I failed miserably with a biohacking gym back in 2020 during COVID. Lost over a million dollars on that." (04:06, Brandon Boeski)

• Lawsuits and Loyalty:

  • Discusses how legal battles reveal your real support system:

    "They teach you a lot. They teach you who your friends are. They teach you who has your back behind your back. And they teach you that anybody can sue you for anything..." (28:50, Brandon Boeski)

• The Fragility of Wealth:

  • Both discuss the illusion of "being set" once you’re a millionaire and how quickly fortunes can change:

    "You start to see how much power money really has at a certain level. But you also see how fragile it is. Like how quickly you can lose most of what you've built." (29:45, Brandon Boeski)

4. Fulfillment, Purpose & Community

Timestamps: 01:23, 08:15, 24:42, 25:18, 40:34

• Redefining Success:

  • Brandon finds more joy mentoring young entrepreneurs in casual settings than making millions:

    "That was actually the most important, impactful thing that I've done in a long time. Like, that was...I left that the happiest that I had felt in a very long time." (08:15, Brandon Boeski)

• Legacy of Impact:

  • Champions building large communities over high-ticket one-on-ones, aiming to "make the most impact and deliver the best result and the best outcome for people." (07:35, Brandon Boeski)
  • Sets goal to build a paid, high-value business community:

    "Get tens of thousands of people into a community, obviously paid...I need to do something that provides value to the world, that makes money and that makes me feel fulfilled." (24:42, Brandon Boeski)

• On Happiness vs. Fulfillment:

  • Advises that true satisfaction comes from ongoing impact, not just income:

    "Happiness is a momentary thing...more happy than not should be everybody's goal. And I think fulfillment usually is where happiness can be found." (40:44, Brandon Boeski)

5. Relationships, Dating & Wealth

Timestamps: 09:05, 09:18, 11:26, 12:00, 14:47, 15:52, 16:33

• Advice to Young Entrepreneurs:

  • Advocates prioritizing building wealth and character before dating seriously:

    "Do not fucking date until you are 25, 26. Make sure they're 25, 26, because that's when they realize life sucks." (09:07, Brandon Boeski)

• Why Most Relationships for High Earners are Tricky:

  • Detailed vetting is essential; wealth attracts insincere partners. Uses mutual friends as "dating strategy," avoids random encounters:

    "It's a lot of sifting. Yeah. But you can figure out who's there for the right and wrong reasons really easily." (11:28, Brandon Boeski)

• Material Gifts and Simping:

  • Strong opinions on 'buying love' and toxic dynamics:

    "The age of just simping over women financially is stupid...you should not have to buy women things to receive love." (13:57, Brandon Boeski)

• Open-minded on OnlyFans/Professions:

  • Non-judgmental if partner is in adult content (with boundaries):

    "If it's genuinely enjoyed and the person doesn't want to do anything else...yeah, I would not write that off..." (16:09, Brandon Boeski)

• Who Pays on the First Date:

  • "Depends who invites." Brandon usually pays unless the vibe's off; will occasionally ensure a gold digger pays "out of principle." (16:33, Brandon Boeski)

6. Lessons from Failure and Reset

Timestamps: 36:12, 37:29, 38:43

• Retirement is Not the Dream:

  • Reflects on a period of early "retirement" as unfulfilling:

    "I wasn't really happy or fulfilled. I wasn't solving new problems. I wasn't creating. I wasn't doing anything meaningful." (38:43, Brandon Boeski)

• Pivot to Coaching:

  • Finds meaning in training others and building a supportive community ("fulfillment usually is where happiness can be found").

7. City Living & Entrepreneur Lifestyle

Timestamps: 31:27, 34:37, 35:11

• Best Cities for Entrepreneurs (2025):
  • Ranks Vegas and Miami as best for opportunity, no state income tax, vibrant business scenes.
  • Hawaii gets a special mention for lifestyle values, not business.

    "The thing that I will say about Hawaii and that I loved about Hawaii is people do not ask you what you do for a living. They ask you what you do for fun." (35:11, Brandon Boeski)

Notable Quotes & Memorable Moments

• "Most people telling you about the stuff, they've never done the stuff." (01:44, Brandon Boeski)
• "A lot of people are chasing revenue, never make money, because they don't understand that eventually you hit diminishing returns." (03:11, Brandon Boeski)
• "That was actually the most important, impactful thing that I've done in a long time." (08:15, Brandon Boeski, on impromptu mentoring in a bathroom)
• "You should not have to buy women things to receive love." (13:57, Brandon Boeski)
• "Happiness is a momentary thing. More happy than not should be everybody's goal. Fulfillment usually is where happiness can be found." (40:44, Brandon Boeski)
• "You start to see how much power money really has at a certain level. But you also see how fragile it is. Like how quickly you can lose most of what you've built." (29:45, Brandon Boeski)

Important Segments & Timestamps

• [01:21] Brandon’s approach to group coaching/impact vs. 1:1 high cost model
• [03:11] Revenue vs. profit; fallacies of business teaching
• [04:06] Lessons from losing a million dollars on a failed gym during COVID
• [08:15] Fulfillment from spontaneous coaching, community building
• [09:05 – 14:47] Dating, relationships, and pitfalls of wealth in romance
• [16:33] First date payment—principles and red flag detection
• [24:42, 25:18] Building community as an entrepreneur’s path to meaning
• [28:50] Lawsuits, loss, finding authentic allies in tough times
• [31:27 – 35:14] Best cities for entrepreneurs, lifestyle reflections
• [36:12 – 38:43] Reflections on retirement, personal fulfillment, and career pivots
• [40:44] Happiness vs. fulfillment—Brandon’s core philosophy

Tone & Language

The episode is informal, straight-talking, sometimes irreverent, and mixes practical advice with raw personal stories. Both host and guest are open about successes, failures, and unpopular opinions, leading to a compelling, relatable dialogue.

For Further Exploration

• Join Brandon’s Community:
  discord.gg/bowsky (Free at time of recording; paywall coming soon)

• Follow Brandon on Instagram:
  [Link as provided in the episode description]

Summary by Digital Social Hour Podcast Summarizer. If you missed the episode, this breakdown will equip you with the key learnings, moments, and themes from Sean Kelly and Brandon Boeski’s powerful, no-BS chat.