Win With Paid Ads – Episode 100: The Hard Truth Behind Building a Business: My 100-Episode Recap

Host: Ashley Brock
Date: January 1, 2026
Theme: Reflecting on 100 episodes with 10 "painful" but vital entrepreneurial lessons on the journey toward an 8-figure business.

Episode Overview

This milestone 100th episode finds Ashley Brock in a celebratory, candid, and reflective mood as she looks back over her podcasting and business growth journey. Ashley delves deep into the "10 painful lessons" that have shaped her from a solopreneur recording awkwardly on Zoom to leading a thriving, multi-million-dollar company. Her honest stories, lessons, and actionable encouragement offer real insight for entrepreneurs at any stage, especially those who want to leverage paid ads to scale—but who might feel overwhelmed or uncertain about what it really takes to build something great.

Key Discussion Points & Insights

1. The Start: From Awkward Beginnings to Confetti-Covered Celebrations (00:00–08:25)

• Ashley reminisces about her very first episode—recorded alone, unsure, and "presenting" rather than conversing.
  • Humorous story: Her husband’s honest feedback—"You sound like you’re presenting to a room of 300 people."
  • Challenges of getting started, especially while pregnant and leaving a stable job.
• Early struggles: Zero revenue, trying to record one episode per day but managing only three in three weeks.
• Key encouragement: "Start before you’re ready. You don’t need fancy equipment. You just need to press record."
  Quote [05:15]:
  “You don’t have to know what you’re doing to get started. You just have to get started.” — Ashley

2. The Power of Consistent Action (08:25–11:55)

• Persistence matters more than perfection.
• It's okay to be messy and imperfect at the beginning; polish comes with time.
• Quote [09:30]:
  "Just show up. That’s how I want to encourage you at the beginning. You can make it pretty later.” — Ashley

3. 10 Painful—but Grateful—Lessons on the Road to $10 Million (11:55–52:45)

Ashley’s structure for each lesson: what happened, why she’s grateful, and how it impacts her and her listeners.

Lesson 1: The Toilet Scrubbing Lesson (12:05)

• Scrubbing toilets at O’Charley’s, manager doubting her.
• Learned to create efficiency and realized others’ perceptions aren’t fact or permanent.
• Quote [13:10]:
  “Someone else’s perception of you does not have to be fact. And it definitely doesn’t have to be fact forever.” — Ashley

Lesson 2: Going to College Alone (15:00)

• Feared solitude, but learned to seize opportunity and trust herself.
• Sometimes, you have to be "first"—but you won’t always be alone.
• Quote [16:05]:
  “You won’t always be alone, but sometimes you will be first.” — Ashley

Lesson 3: Getting Underpaid (17:45)

• Realized a less-experienced coworker earned much more.
• Chose to work harder and look beyond the moment; developed appreciation for growth and value over time.
• Cultivated resilience and an abundance mindset.

Lesson 4: Marriage Challenges & Counseling (21:10)

• Open talk about marriage trouble, counseling, and investing five-figures into therapy.
• Underlines money as a frequent stressor—and how helping clients succeed means relieving that burden.
• Key insight: Every relationship (personal or business) will face challenges; embrace growth.
• Quote [24:45]:
  “Every relationship will struggle. Things are hard, and things can change. And people can change, too.” — Ashley

Lesson 5: Losing Friends and Shifting Circles (28:25)

• Pain of losing friends (“some people are for a season and for a reason”).
• Stopped chasing universal approval, focused on mutual value in relationships (clients and friends).
• Embraces qualifying her circle—and by extension, her clients.

Lesson 6: First Paid Ads Failure (32:32)

• Early ad campaigns flopped; spent thousands before seeing returns.
• Empathy from firsthand experience—understands her clients’ risk and doubts.
• Biggest risk led to the biggest reward (first 10:1 return ROI).
• Quote [34:05]:
  “Every time I risk more, we have a bigger opportunity for a bigger reward.” — Ashley

Lesson 7: Begging for Money: Chase Bank Story (36:37)

• Humbling moment, pitching her business vision to a bank rep for funding.
• Importance of "going deep before fruiting”—building roots first.
• Paying the price before expecting the payoff.

Lesson 8: First Client Who Wanted to Cancel (39:46)

• Early 100% success rate gave way to a hard lesson—some clients will never be happy.
• Not everyone is a fit, some clients are negative or non-committal.
• Led to developing a stronger client qualification process and clarity on whom she wants to serve.
• Quote [44:08]:
  “You can never make 100% of people happy… some people just are not the right people.” — Ashley

Lesson 9: Messing Up in Front of the Team (47:06)

• On extreme ownership and setting a culture of vulnerability and accountability.
• Her apology modelled leadership, team followed suit when errors happened.
• Encourages mistakes as evidence of real effort.
• Quote [48:45]:
  “If you’re not making a couple of mistakes, you’re probably not challenging yourself enough and taking enough action.” — Ashley

Lesson 10: Letting Team Members Go (50:15)

• Painful but necessary: letting valued team members go for the good of the whole.
• Importance of hard conversations, intentional hiring, and accountability.
• Team and clients see, feel, and depend on leadership standards.
• Quote [51:03]:
  “The precedent that you set for what is and is not allowed is demonstrated by what you do allow and the actions that people see.” — Ashley

Memorable Moments & Motivational Highlights

• The confetti incident (03:22): Playful, messy celebration in studio—"There’s confetti everywhere! I am not sure who’s cleaning this up…"
• Admission of imperfection (07:30):
  “I just messed up right there. Like, you just don’t stop when you mess up. You just keep going.”
• Courage to be selective (44:45):
  “For those people, I am going to say, here’s who it’s for and not for, and gladly and kindly say, this is not for you. And that is such a gift.”
• On progress and growth (53:12):
  “Whether it’s your hundredth ad, your hundredth dollar, your hundredth episode, every single time that you show up, even if you mess up, that’s how you can level up.”

Timestamps for Key Segments

| Timestamp | Segment Summary | |-----------|------------------------------------------------------------------| | 00:00 | Introduction; 100th episode celebration; reflections on starting.| | 05:15 | Encouragement to start before ready, “just press record.” | | 11:55 | Transition into “10 painful lessons”—the core of the episode. | | 12:05 | Lesson 1: O’Charley’s, toilet cleaning, and self-worth. | | 15:00 | Lesson 2: Going to college alone, creating your own support. | | 17:45 | Lesson 3: Being underpaid, valuing your own growth. | | 21:10 | Lesson 4: Marriage challenges; investing in counseling. | | 28:25 | Lesson 5: Losing friends and redefining your circle. | | 32:32 | Lesson 6: Paid ads failure, risk and reward. | | 36:37 | Lesson 7: Begging for money—a lesson in roots over fruit. | | 39:46 | Lesson 8: First difficult client; qualifying customers. | | 47:06 | Lesson 9: Team mistakes, extreme ownership. | | 50:15 | Lesson 10: Letting go of team members; leadership and standards.| | 53:12 | Final words: All challenges make you better; keep showing up. |

Final Takeaways

• Embrace Imperfection: Every journey starts with messy, awkward steps—get started anyway.
• Be Consistent: Progress, not perfection, is the driver of growth.
• Expect—and value—challenges: Each difficult lesson makes you and your business stronger.
• Be selective: Success means serving the right people and forming the right team.
• Lead with ownership: Admit mistakes and improve quickly—your team will mirror your standards.
• Keep Going: The only real regret is not starting sooner.

Ashley’s recurring message:

"You just have to get started. Show up, even when you mess up—that’s how you level up." (05:15, 53:12)

Want to go deeper?
Ashley invites listeners to join her Win with Paid Ad Challenge for hands-on support and live business feedback. For business owners who want to be seen, make an impact, and win sooner with the right advertising strategy, her advice is clear: the journey is tough, but it’s absolutely worth it.