Podcast Summary: The Messy Parts with Maryam Banikarim

Episode: Rafat Ali Plays the Long Game: This Internet Pioneer Says You Should Stop Rushing Your Career
Date: December 1, 2025

Overview

In this deeply candid episode, Maryam Banikarim sits down with Rafat Ali, founder and CEO of Skift, to unpack the non-linear, “messy” journey behind apparent career success. Rafat opens up about culture shock, self-doubt, legacy, and why he champions patience over the “quick win” mentality. The conversation is raw, therapeutic, and packed with wisdom for anyone questioning their next step or trying to find meaning amid professional chaos.

Key Discussion Points & Insights

1. The Hidden Messiness Behind Career Highlights

• Rafat’s Journey: From India to Indiana, switching from computer science to journalism, building paidContent, and then Skift.
• LinkedIn vs. Reality: “If I look at it on LinkedIn, it’s like a hockey stick up and to the right…And yet we know there were many moments that were messy.” (Maryam, 04:32)
• Shared background of being outsiders navigating expectations from immigrant families.

2. Navigating Parental Pressure and Cultural Identity

• Parent Expectations: Rafat followed his parents into engineering but soon realized his draw toward creativity.
• “Like all Iranians, they want us all to be computer scientists, doctors or engineers.” (Maryam, 01:40)
• “I used to stammer till I was 17…So my vocabulary as a result increased…I would express myself in writing.” (Rafat, 03:53)
• Discovery of a profound letter from Rafat's father, emphasizing perseverance and self-reliance ([07:12]).

3. Early Career Pivots and Landing in the US

• Adjustment Challenges: Culture shock, isolation, learning US culture through mass media, and building networks in unexpected places.
• “For me, cable TV…literally, this sounds so ridiculous…but to me, US was Baywatch.” (Rafat, 05:01)
• The importance of having mentors and guides in adapting to new cultures.

4. The Power of Patience and “Playing the Long Game”

• The Two-Year Rule: “If you’re starting a new business, give it two years. If you’re starting a new relationship, if it lasts two years, that’s great.” (Rafat, 00:07 & 09:40)
• Compound Careers: Staying in one place to build deep skills and networks, rather than quick job-hopping.
• “Career compounding…put your roots, hone your craft. When you’re ready to fly, you’re in exponential position.” (Rafat, 15:43)

5. From “Nice-to-Have” to “Must-Have”

• Product Mindset: The journey of making Skift indispensable through daily value and trust.
• “Your goal…has always been how do we become of daily utility value to our readers? The biggest thing is from nice to have to must have.” (Rafat, 11:30)
• Importance of habits and email intimacy in media business.

6. Influence Over Money

• Choosing Influence: Rafat consistently prioritized impact and sector influence over financial gain.
• “I wanted to be the most influential force in a specific sector.” (Rafat, 12:22)
• “Money for me is…not important. If I don’t have the money now, I’ll figure out ways to get it later.” (Rafat, 23:17)
• Delayed gratification as a value learned from his upbringing.

7. Dealing with Setbacks, Resets, and Burnout

• Crisis Stories: COVID nearly shuttered Skift and the Silicon Valley Bank collapse threatened its survival.
• “We came three weeks from running out of money, and somehow we crawled our way out of it without raising any external money.” (Rafat, 29:22)
• Coping Mechanisms: Work, team support, compartmentalization, and taking mental health breaks.
• “For me, it was work, but also playing off the energy of my immediate team.” (Rafat, 30:56)

8. On Legacy and Family

• Physical Legacy: Bringing family to events to let them see the impact, especially for his mother and children.
• “My parents did not understand what I did since I left…When I brought her to the conference…it was very emotional for her.” (Rafat, 26:28)

9. Advice for the Next Generation

• On Career Choices: He wouldn’t recommend journalism now without specialization or entrepreneurship component.
• On parenting: encourages his son to follow interests in aviation but is realistic about the need for direction.
• “Don’t be in a hurry. This book…‘100 Year Life’ was very influential for me.” (Rafat, 33:08)

Memorable Quotes & Moments

• On Longevity:
  “One of the biggest lessons I’ve learned in hindsight, again, the power of longevity, both in terms of my own company…Dog years.” (Rafat & Maryam, 15:18-15:31)
• On Taking the Long Way:
  “I always want to take the long way only because it’s just a lot more interesting.” (Rafat, 12:45)
• On Resilience and Setbacks:
  “Every setback can be an opportunity, is…an opportunity for a reset or something better comes off it a hundred percent.” (Rafat, 29:03)
• On Influence vs. Likeability:
  “I don’t want people to like me…But respect. That outsider looking-in respect and understanding that as a journalist, if I have an opinion, I’m speaking from a position of knowledge.” (Rafat, 24:35)
• Summing Up Life Advice:
  “In the end it all works out. After a lot of mess. But if it’s still a mess, that means it’s not the end.” (Rafat, 28:20)

Timestamps for Key Segments

| Timestamp | Segment | |-----------|------------------------------------------------------| | 00:07 | Two-year Rule for Business and Life Decisions | | 03:53 | Overcoming Stammering, Early Writing as Expression | | 04:51 | Culture Shock Moving from India to Indiana | | 07:12 | Life Advice from Rafat’s Father’s Letter | | 09:40 | Career Longevity and Incremental Progress | | 12:22 | Choosing Influence over Money, Niche Focus | | 15:43 | Compound Careers over Job-Hopping | | 18:12 | Supporting Employee Growth, Career Pathways | | 20:05 | Future of Media and Journalism Advice | | 21:41 | Passion vs. Profit in Career Decision | | 23:17 | Money, Delayed Gratification, and Equity | | 26:28 | Sharing Success and Legacy with Family | | 29:22 | Skift’s Close Calls: COVID and Banking Crisis | | 33:08 | “Don’t be in a hurry” and the 100-Year Life Concept | | 34:49 | Visualizing Success and Manifestation |

Rapid Fire Tips & Takeaways

• Before 35? Travel as much as you can. (32:44)
• Career Myth to Ditch: “If you jump from place to place you will get a higher salary? I think that’s a…myth.” (32:50)
• Job Search Advice: “Don’t be in a hurry.” (33:08)
• Handling Setbacks: Every personal and professional setback often opens space for growth or something better.

Tone & Atmosphere

• The conversation is forthright, warm, and occasionally self-deprecating, with both Maryam and Rafat sharing vulnerable stories from their immigrant, outsider upbringings.
• The episode weaves between deep reflection and practical wisdom, steering clear of clichés by offering firsthand, sometimes raw, perspectives.
• Strong sense of camaraderie and “therapy session” humor as both admit to compartmentalization and internal chaos behind polished CVs.

Concluding Insight

At its core, this episode champions the virtue of patience, deep work, and authenticity over outward markers of “success.” Rafat Ali’s story is a guide not just for entrepreneurs or media insiders but for anyone stuck between the highlight reel and the messy middle. As he puts it:

“If it’s still a mess, that means it’s not the end.” (28:20, Rafat Ali)

[End of Summary]