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Episode #83: The Questions I Ask Before Investing in Rooms

Host: Ashley Brock
Date: August 28, 2025

Overview

In this episode, Ashley Brock dives into her personal decision-making process when choosing which masterminds, groups, or mentorship "rooms" she invests in. Sharing practical questions and mental filters, Ashley explores how business owners can evaluate rooms, mentors, and investments that accelerate growth and avoid stagnation. This episode functions as the foundation for an upcoming series where Ashley will break down the results and insights she’s gained from specific investments—with an emphasis on actionable criteria anyone can apply immediately.

Key Discussion Points & Insights

Introduction & Upcoming Content

• Ashley sets the scene by discussing new YouTube-exclusive content, including styling sessions with Charla and Emily and a documentary-style batch content day with video specialist Ryan ([00:00 – 03:27]).
• She introduces the series focus: the importance of "rooms"—mastermind groups, challenges, events—and how the right rooms can compress your learning curve ([03:27 – 05:05]).

The Four (+1) Questions to Ask Before Investing in a Room

Ashley shares her personal checklist for evaluating mentors, masterminds, or coaching programs:

1. Are They Investing in Themselves? ([05:20])

“If they are not investing to be in other rooms with other people, then I’m probably not gonna move forward.” – Ashley ([05:32])

• Look for leaders actively expanding their horizons, not just selling access to theirs.

2. Have They Failed More Than I Have? ([06:05])

• Ashley seeks out mentors who have weathered more failures—this depth means resilience, adaptability, and practical experience.

3. Have They Succeeded Beyond Only Themselves? ([06:30])

“Is the strategy they’re using…working for their clients, not just for them?” – Ashley ([06:37])

• It’s not enough for a mentor to be self-made—their approaches must create repeatable success stories for others.

4. What's the Cost of Not Doing This? ([08:06])

“Price is what you pay and value is what you get. Cost is what happens if you don’t pay.” – Ashley ([08:15])

• Beyond just money, Ashley considers opportunity costs: lost momentum, lost speed, and what it means to stagnate.

5. Are There Too Many Cooks? (Bonus: The Championship Team Analogy) ([10:45])

“You wouldn’t hire four head coaches... what you need is a head coach, a defensive coach, an offensive coach… each own their own lane and together, they create a winning team.” – Ashley ([11:01])

• She pushes against spreading yourself thin across too many "advisors" in the same field. Instead, assemble a specialized, non-overlapping "coaching team."

Applying the Filters: Practical Scenarios

• Ashley outlines how she invested in video content expertise—not just because it was fun, but because it served a clear missing link in her "championship team," multiplying the impact of her paid ads program ([12:40 – 13:32]).
• She warns against "choice overload" and celebrates the value of curated guidance:

“Finding the right room…saves you sanity. We talk about saving money… but you need someone to help you eliminate that choice overload.” – Ashley ([17:24])

Notable Quotes & Memorable Moments

• On misleading "proven" claims:

  “So many people get a result one time and they’re like ‘yay, I can teach this.’ I’m like, you have not experienced what time can teach you.”
  — Ashley ([07:19])

• On progress and going through every step:

  “If you want to get from the first floor to the tenth floor, you have to go through the second, third, fourth... You will not be prepared to actually lead on that tenth floor if you haven’t been.”
  — Ashley ([14:22])

• Skin in the game:

  “People who have skin in the game… often give better advice. When you win, we win. Because my whole business is built on you winning with paid advertising.”
  — Ashley ([21:17])

Research & Data Callouts

• Harvard Business Review Study:
  Entrepreneurs who align decisions with their business stage are 3.6x more likely to scale successfully ([15:36]).

• CB Insights:
  42% of startups fail because they build something the market does not want ([16:33]).

• Edelman’s Trust Barometer:
  65% of people trust peers with direct experience more than influencers ([19:16]).

• Entrepreneurship Mentoring Research:
  Founders paired with active business owners saw a 27% higher success rate ([22:04]).

Action Steps & Takeaways

Ashley recommends listeners ask themselves these pivotal questions before any investment:

• Does this person/investment align with my current stage and goals?
• Have they “tested” and “proven” their approach with people like me?
• Am I avoiding information/choice overload by getting the right people for the right business areas?
• Does this advisor have recent, relevant experience?
• Do they have “skin in the game” that ensures their incentives align with my success?

“Ask yourself those five questions and it’s really going to help you as you make investments that can really elevate you and speed things up. I’m grateful I’ve done that in my business, too.” ([23:52])

Closing & What’s Next

Ashley previews the coming episodes, which will feature specific rooms she’s invested in—including short-term rental/ad room strategies and what she learned from being in a room with Alex Hormozi.

“Get ready because there’s some good stuff coming on these next few episodes about rooms that we’ve invested in and what we’ve learned. Can’t wait to see you.” ([25:20])

Timestamps for Key Segments

| Timestamp | Segment Description | |------------|----------------------------------------------------------------------| | 00:00 | Welcome, podcast premise, YouTube content highlights | | 03:27 | Introducing the “rooms” & upcoming mini-series | | 05:20 | The four (+1) questions to ask before investing in a room/mastermind | | 10:45 | Championship team analogy—combining experts vs. duplicating roles | | 12:40 | Video content investment as strategic team building | | 14:22 | The necessity of progressing through every business stage | | 15:36 | HBR research: decisions aligned to business stage | | 16:33 | CB Insights: why startups fail | | 17:24 | Value of curated expert rooms vs. choice overload | | 19:16 | Edelman’s Trust Barometer: proof vs. popularity | | 21:17 | “Skin in the game” filter | | 22:04 | Mentoring stat: 27% increase with active business owner mentors | | 23:52 | Recap of five decision-making filters | | 25:20 | Preview of coming episodes |

For listeners serious about accelerating their business through strategic paid advertising, Ashley’s filters provide an essential blueprint for choosing the ‘right’ rooms—and avoiding costly missteps with the wrong ones.