Escaping the Drift with John Gafford

Episode: From Underachiever to Entrepreneurial Success: Robert Glazer's Journey and Wisdom
Guest: Robert Glazer
Date: October 28, 2025

Episode Overview

This episode features Robert Glazer, successful entrepreneur, best-selling author, and founder of Acceleration Partners. Host John Gafford explores Glazer’s journey from chronic underachievement to recognized business leader. The conversation delves into finding one’s personal core values, the importance of authentic communication, and how setbacks become superpowers. The two share anecdotes about entrepreneurship, writing, and the essential tools required to “escape the drift” in life and business.

Key Discussion Points & Insights

1. Robert Glazer’s Early Years: From Underachiever to Entrepreneur

• Early Underachievement:

  • School report cards noted he was below potential due to lack of engagement.
  • “I just wasn't super interested in what they were teaching in school... I was running a little Now and Later candy business on the side until my grandmother shut it down.” [03:56 - Glazer]

• Discovery of Entrepreneurial Talents:

  • Ran businesses in college, like moving and candy sales, that weren’t recognized by traditional institutions.
  • Realized his real strengths were in building things and marketing.
  • “Once I fell into creating things and entrepreneurship, I knew I had my home.” [02:37 - Glazer]

2. Newsletter Growth & the Power of Consistency

• Origin of ‘Friday Forward’:

  • Started as a Friday note to his team to improve communication and morale.
  • Grew organically as people shared it; eventually evolved into a formal newsletter.
  • “I have over 1200 people who are on the paid version of that now [on Substack]... I'm playing the odds out of hundreds of thousands of people, like, perfect message, perfect time, and it made a difference for them.” [07:15 - Glazer]

• Advice on Creating Content:

  • Stay consistent and write often. Don’t overthink or draft endlessly.
  • “It's a five minute note every week... If you were to write more often and shorter and just get it out there, you would have a little more escape velocity.” [11:16 - Glazer]

3. Writing and Publishing Books: Authenticity and Market Realities

• Approach to Book Writing:

  • Prefer concise books that are actionable and can be finished in an hour or two.
  • “My bestselling book, you can read them in an hour to an hour and a half... It gets to the point.” [13:16 - Glazer]
  • Advocates authors narrate their own audiobooks: “I think it’s weird when you don’t…you have a brand and a voice and I’m used to hearing it.” [13:59 - Glazer]

• The Publishing Business:

  • Shared experiences between self-publishing and traditional publishing.
  • “Publishers are a little like venture capitalists… They make some bets and if they start to pay off, they double down.” [17:33 - Glazer]
  • On book marketing: “Every time we do it… we did a hundred things that were different and 10 out of the hundred worked.” [18:54 - Glazer]

4. Core Values – The Basis for Decision Making & Fulfillment

• Upcoming Book – Core Value Discovery via Parable:

  • Shows how life crises expose the importance of personal core values.
  • “I have a formula to figure out your personal core values that I think is very different… These things show up for us in all aspects of our life and our leadership.” [20:21 - Glazer]

• Connection of Pain and Purpose:

  • Personal struggles like being picked on or criticized as a child often become adult superpowers.
  • “Purpose and pain live very close to each other... Every weakness is a strength overused in most cases” [23:43 - Glazer]

• Defining and Living Core Values:

  • “My dominant core value is find a better way and share it. Health and vitality, self reliance… respectful authenticity and long term orientation.” [28:26 - Glazer]
  • Advises listeners to identify what behaviors boil their blood and reverse-engineer personal values.

5. Authenticity, Networking, and Mentorship

• Time is Precious:

  • Strong aversion to people who waste time; tie this to his own history of “drifting.”
  • “How you do anything is how you do everything... I'd rather have you steal my wallet than waste my time.” [30:03 - Gafford]

• Rules for Helping Others:

  • “If you ask something of me and you're asking me to do more work than you're willing to do yourself, then I don't really want to help you.” [35:03 - Glazer]
  • Prefers helping “the right horses”—people who are proactive and receptive.

6. Cultural Trends: Post-COVID Apathy & the Future of Work

• Shifts in Attitude:

  • Observes increased apathy post-COVID; foresees more jobs disappearing if engagement doesn’t improve.
  • “You should be learning, you should kill yourself in your 20s... You will then be able to unfairly monetize [that expertise] in your 30s and beyond.” [38:25 - Glazer]

• Social Media and Unrealistic Expectations:

  • Young people pressured by images of quick success, often “playing the wrong game.”
  • “There's an amount of success and money after which it doesn't make you happier... 40% more than whatever they had… more was the answer.” [41:28 - Glazer]

7. Memorable Metaphors & Anecdotes

• The Waiter Without a Pen:

  • Both share stories of waiters risking tips for the sake of a “memory trick,” paralleling how people often chase the wrong validation or “game.”
  • “At no point in any Yelp review... does it say, holy crap, the waiter had an amazing memory.” [42:28 - Gafford]

• Being an Underachiever in School:

  • “I was the C student that the A students ended up working towards.” [47:36 - Glazer]
  • Success often blooms outside of standardized pathways.

Notable Quotes & Memorable Moments

• On Discovering Your Strengths:

  • “A decade of underachievement led to some guilt and some overachievement... I realized, you know, I was good at building businesses and marketing in general, and those are things that school doesn't super reward.” [02:37 - Glazer]

• On Authentic Communication:

  • “[Friday Forward]... It's that message hit them at a... perfect message, perfect time, and it made a difference for them.” [07:15 - Glazer]

• On Writing & Content Creation:

  • “So much of people's problem with writing... is thinking, overthinking, saving the draft forever...” [11:16 - Glazer]

• On Time and Respect:

  • “I'd rather have you steal my wallet than waste my time. I replace the wallet easily, but the time, I can't.” [30:43 - Gafford]

• On Pain and Purpose:

  • “Purpose and pain live very close to each other... Every weakness is a strength overused...” [23:43 - Glazer]

• On Playing the Right Game:

  • “At no point in any Yelp review... does it say, holy crap, the waiter had an amazing memory.” [42:28 - Gafford]
  • “They're trying to win the wrong game.” [43:44 - Gafford]

Key Timestamps

• Entrepreneurial Beginnings: [02:37]
• Newsletter Origins and Growth: [06:57 - 10:18]
• Writing Process and Audiobooks: [13:16 - 16:23]
• Publishing Realities: [17:01 - 18:54]
• Core Values Discussion: [20:21 - 28:26]
• Childhood Pain to Adult Superpower: [23:43]
• Mentorship & Time Management: [31:14 - 36:49]
• Post-COVID Apathy: [38:13 - 40:03]
• Social Media, Success, and Money: [40:39 - 41:28]
• Waiter Pen Anecdote (“Playing the Right Game”): [42:26 - 44:18]
• Defining Current Goals: [45:49]
• School Performance Relates to Later Success: [47:36 - 48:34]

Additional Resources

• Robert Glazer’s Website & Newsletter:
  • robertglazer.com (Friday Forward newsletter)
• Latest Book:
  • compass-within.com

Conclusion

Robert Glazer’s episode is a masterclass in reframing setbacks as strengths, identifying authentic core values, and avoiding the drift of mediocrity. For anyone feeling stuck or searching for purpose, Glazer’s actionable advice, candid stories, and relatable metaphors provide a clear pathway to both personal and professional transformation. As always, Gafford’s straightforward style and incisive questions keep the focus on practical, real-world application of success strategies.