The Learning Leader Show with Ryan Hawk

Episode 668: Brian Kelly (The Points Guy) – Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel
Release Date: December 29, 2025
Host: Ryan Hawk | Guest: Brian Kelly (The Points Guy)

Overview

In this engaging episode, Ryan Hawk sits down with Brian Kelly, founder of The Points Guy, to discuss how Brian transformed a childhood interest in frequent flyer miles into a global media empire. The discussion ranges from Brian’s relentlessly resourceful upbringing and vision-driven mindset, to the nuts and bolts of scaling a business, the challenges of leadership, the importance of hiring well, and practical travel and career advice. The conversation is candid, personal, and filled with actionable insights for aspiring leaders, entrepreneurs, and anyone looking to “win at travel” and life.

Key Discussion Points & Insights

1. Early Roots: Resourcefulness, Family, and the Origin of The Points Guy

(Timestamps: 02:19–06:12)

• Early Tech & Travel Hacking:

  • Brian was a self-taught computer whiz by age 8, managing his family’s early internet connections and experimenting with eBay in the 90s.
  • At 12, he began booking travel for his father—his first “side hustle”—which introduced him to points and miles.
    • “[My dad] was paying me 10 bucks a booking and it took me like 60 seconds to do.” (Brian Kelly, 03:31)
  • Family travel booked using points to the Caribbean at a cost less than driving to the Jersey Shore was a pivotal moment.

• Vision and Manifestation:

  • Growing up in a middle-class, humble family, Brian was “obsessed with exploring the world” and envisioned abundance.
  • He credits visioning—cutting out Mercedes brochures as a kid—as fueling ambition and taking “the smaller steps to actually achieve it.” (06:27)
    • “Manifesting alone is not going to make you wealthy, but I do believe being able to vision what it looks like and taste it helps you take the smaller steps.” (Brian Kelly, 06:27)

2. Building The Points Guy: From Blog to Media Empire

(Timestamps: 07:17–15:46)

• Unexpected Scale:

  • Brian never pictured TPG growing beyond a small operation—“I never wanted to make the points guy big.” (07:48)
  • Key differentiator: Translated the complex world of points and miles for everyday people, adding creativity and accessibility.

• The Power of Media:

  • Leveraged his public speaking skills and media appearances to build brand recognition, outpacing competitors who kept things insular.

• The Decision to Sell:

  • Documented the rise of affiliate marketing (2011) and the “gold rush” in the blogosphere.
  • Sold The Points Guy to Bankrate in 2012 for $28 million, motivated partly by industry uncertainty and a flood of copycat blogs.
    • “When they offered me $28 million to buy this blog, I kind of had this negative mindset over where the industry was going…so I decided to sell.” (Brian Kelly, 13:44)
  • Stayed on as CEO and later transitioned to a brand visionary role, eventually working under Red Ventures after Bankrate’s acquisition.

• Work-Life Shifts:

  • Stepped down as CEO during the pandemic after burnout—company had surpassed 100 employees and he was both frontman and manager.
    • “[My employers said] we’ve been waiting for you to say that, you don’t need to be CEO. We have plenty of smart people managers…It was an aha moment.” (Brian Kelly, 17:59)
  • Advice: “People are not mind readers...the more vulnerable I was, saying ‘how can we work together?’ – It has turned out to be such a blessing.” (Brian Kelly, 17:59)

3. Leadership, Hiring, and Growth

(Timestamps: 27:06–32:14)

• Scaling and Letting Go:

  • Learned to hire smart people and trust them, even though perfectionistic tendencies made delegation difficult.
  • Mistake: Focusing too much on mistakes instead of celebrating wins.
    • “If I could do it all back over again…I’d be much more about highlighting wins.” (Brian Kelly, 27:42)

• Truth-Telling and Vulnerability in Leadership:

  • Importance of honest conversations, both as a boss and with colleagues.
  • Hiring: Looks for candidates who are vulnerable about their failures and leadership challenges, rather than just touting successes.
    • “The interview process is too…everyone is BSing way too much. Stop telling me the wins…really just diving deep into vulnerable moments about their leadership.” (Brian Kelly, 29:17)
  • Charisma in interviews can be misleading—looking for substance over personality.

4. Wealth, Motivation, and Investing

(Timestamps: 32:14–38:47)

• Living the Dream (but with Imposter Syndrome):

  • Despite success, Brian sometimes still feels like “do I…are my bills paid?”
  • Finds grounding and joy in investing in a home/farm, noting the value of creating environments that lower stress and foster happiness.

• Why Keep Working?

  • The drive doesn’t dissipate with financial security; Brian invests in startups not just for returns but for fun, relationships, and to leverage his experience.
  • Notable investment: Bilt, now valued at $11B—Brian is an advisor and early investor.
    • “Angel investing has basically become an addiction.” (Brian Kelly, 36:43)
  • Feels useful contributing as an advisor, not CEO—“I’m a racehorse, put me in the race…just not seven days a week.” (Brian Kelly, 37:16)

5. Attributes of Relentless, Sustained Leaders

(Timestamp: 37:00–39:33)

• Key Trait: Relentlessness

  • Successful leaders he admires (e.g., Encore, Michael from Cardless) are “relentless in pushing for excellence.”
  • Bold thinking, continuous action; unable to simply “chill” once success is achieved.

• Balance & Parenthood:

  • After achieving business success, Brian prioritized fatherhood, becoming a single dad by choice.
  • Makes deliberate choices to work from home and remain present for his young children.

6. Travel Advice and Rewards Strategy

(Timestamps: 41:31–45:05)

• Favorite Destinations:

  • Antarctica (just visited with family and kids), South Africa (“Ultimate soul-refreshing trip”).
  • Practical tip: Leverage airline point specials, e.g., Delta’s ongoing deals to Australia and South Africa.

• Travel Habits:

  • Still flies commercial, often prefers premium cabins on top airlines over private jets.

• Credit Card Points Advice:

  • For entrepreneurs: Use Chase Sapphire Reserve Business for 3x points on internet advertising—“Points are like tax-free income when you think about it.” (Brian Kelly, 44:24)

7. Career Advice for Aspiring Leaders

(Timestamps: 46:09–47:43)

• Mentorship Matters:

  • Prioritize working for great people over working for great companies.
    • “Find someone at that company that you connect with…find that hiring manager that you feel is on an upward rise and that you can learn from.” (Brian Kelly, 46:09)
  • Be proactive, network internally, seek face time with senior leaders—being visible counts when it comes to progression.

• Final Recommendations:

  • Read Brian’s book, “How To Win At Travel” for more tips.
  • Follow Brian Kelly on Instagram and sign up for his weekly newsletter at ThePointsGuy.com

Memorable Quotes

• On Vision:

  • “Manifesting alone is not going to make you wealthy, but…get close to it, helps you take the smaller steps to actually achieve it.” (Brian Kelly, 06:27)

• On Delegation and Growth:

  • “If I look back at my time as CEO, I was a tough boss…because as a founder…it’s so personal.” (Brian Kelly, 27:06)

• On Advice to Leaders:

  • “Always leave on good terms. The network is smaller than you think. Burning bridges may feel good…but it will come back to haunt you.” (Brian Kelly, 19:55)

• On Leadership Attributes:

  • “Relentlessness is the first thing that comes to mind…thinking boldly.” (Brian Kelly, 37:16)

• On Career Progression:

  • “Find someone at that company that you connect with…that you can learn from. Stop focusing on the company and look at that manager…” (Brian Kelly, 46:09)

Notable Moments & Timestamps

• Brian gets hired by his dad as a travel agent and books his first family points trip – 03:34
• The pivotal moment selling TPG and navigating industry shifts – 13:44
• Brian’s burnout and transition from CEO to visionary role – 16:51–17:59
• The transformative power of media mentions (New York Times) – 21:11
• Lessons learned (and mistakes made) in scaling leadership – 27:06–27:42
• Career advice for new grads: seek great mentors/managers – 46:09

Closing Thoughts

Brian Kelly’s journey is a masterclass in resourcefulness, vision, and adaptability. From his earliest days as a computer-savvy kid to pioneering the points-and-miles space for mainstream audiences, he’s built lasting value by staying true to his strengths, building relationships, and continuously adapting. In both business and life, he advocates for honest communication, investing in great environments (and people), and never shying away from thinking bigger than what feels comfortable.

Follow his work at ThePointsGuy.com, on Instagram @BrianKelly, and check out his book How to Win At Travel for more.