Ep 36: How We Bootstrapped Our First Million Dollars
Release Date: 10/20/2025
The 30-Day Year Podcast
In this episode of the 30 Day Year podcast, Dave and Jacq Conway reflect on the past year and discuss the importance of finishing strong, both in business and in life. They share personal stories about their own growth, highlighting how 2025 was a year of learning, self-discovery, and professional development. Jacq talks about her focus on mastering her craft and building consistency, especially around content creation, while Dave opens up about overcoming his own challenges with producing content, even seeking counseling to move past creative blocks. Dave and Jacq stress that finishing what...
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In Episode 43 of The 30-Day Year Podcast, Dave and Jacq Conway open the door to the most defining conversation of a person’s life: finding the energy, identity, and defined direction behind your purpose. This episode isn’t simply about “finding your why.” It’s about learning to recognize that electric sensation inside you… the one that tells you when you're alive, when you’re useful, and when you’re finally doing the work you were meant to do! Dave and Jacq take listeners through the search, the pivot, the awakening, and the service that defines a life of purpose. Their...
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Your environment is more important than you think. In fact, it could be the hidden factor keeping you stuck, even if you are doing everything else right. In this episode of the 30-Day Year Podcast, Dave and Jacq Conway unpack what they call The Environment Advantage and show you how to design a “habitat” that actually supports your goals instead of fighting them. In this conversation, you will discover: The 7 core environments that shape your income, attitude, and inner peace... The sneaky way your environment is making over 90 percent of your decisions for you… while you still think...
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In episode 41 of the 30-Day Year, “Team Building: Wins, Losses, and Learning,” Dave and Jacq Conway unpack what really happens behind the scenes when you’re trying to build a strong, reliable team, and Jacq spills the beans and reveals her secrets for building a high-performing team! She breaks down the Conway values and expectations framework, and walks through her recent hiring process that filtered 130 applicants down to one great fit. If you’ve ever said, “I can’t find good people,” or felt frustrated with hiring, and you want to protect your brand and design a small but...
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In this special role-reversal episode, Dave Conway turns the tables and interviews his wife and CEO of Conway Mentorship, Jacq Conway. Get ready for a lively Q&A and a deeper conversation about leadership, fearlessness, higher standards, and what really drives the growth of Conway Mentorship. This is the side of Jacq you rarely see, and she really opens up. In this podcast episode you’ll discover: The surprising season that completely recharges Jacq’s energy, and what it reveals about her personality.... The single event that “shook her up like nothing else”... and how it changed...
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Ready to go behind the scenes and get to know Dave better? In this playful and rapid-fire episode of The 30-Day Year Podcast, we get the real, human, funny side of the man behind the mindset. No preparation. No script. Jacq Conway starts this episode with a sly grin and asks… smiling, “Hey Dave… want to play a game?” What followed was 15 rapid-fire questions that revealed: His one vice he wishes he could quit (and no, it’s not coffee)... His controversial airplane seat choice… The only compliment that ever truly landed… The decade of music he swears is the greatest of all...
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In this liberating episode of the 30-Day Year Podcast, Dave and Jacq Conway reveal that debt is nothing to be afraid of. Nor is it something to feel ashamed or embarrassed about. Debt is not a character flaw. It is simply a habit. And like all habits, it can be changed. You’ll discover: The real definition of debt, and how to release any shame or guilt around debt… How to raise your confidence that you CAN pay off your debt faster and easier than you ever thought possible and get on the right side of compounding… The mindset that helped one of Dave’s clients wipe out $70k in debt...
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Most people see failure as the end. Dave and Jacq Conway see it as the beginning. In this powerful episode of The 30-Day Year Podcast, Dave shares how failure became his greatest teacher… from flopping on camera to getting crushed at the pool hall. Together, he and Jacq unpack how persistence, desire, and daily self-reflection can turn setbacks into stepping stones. If you’ve ever felt defeated by rejection or ready to give up on your goals, this inspiring conversation will show you how to learn from failure and use it as fuel for growth! You’ll discover: Why failing is actually just...
info_outlineWant to learn the TRUTH about how Dave and Jacqueline Conway built their first million-dollar year… without loans, investors, or fancy systems?
In this exciting and inspiring episode of The 30-Day Year Podcast, Dave and Jacq Conway take you behind the scenes and share the real story of how they bootstrapped their business from zero to $1.4 million! They reveal how focus, faith, and a simple $30 whiteboard became the foundation of their success.
Learn the simple systems that work in any industry… how to build momentum through sales, how to pivot when life throws curveballs, and how to “keep the main thing the main thing.”
What You’ll Learn
- The real definition of bootstrapping a business…
- How Dave went from carpenter to coach in just 31 months…
- Why leaving Bob Proctor’s team was the scariest but one of the best decisions he ever made…
- The “Road to 100” whiteboard that drove $1 million in sales!
- How to pivot under pressure and turn setbacks into momentum…
- The truth about sales, service, and the real path to true freedom…
And much more!
Listen now to hear the full story and discover the practical steps that took them from making $5K a month to earning over $100K per month and beyond!
Free Resources:
- Visualization Checklist
- How to Set 30-Day Year Goals Guide
- 21-Day Money Momentum Challenge
- Money Mindset Worksheet
Timestamps:
00:00 – Introduction & Episode Preview
01:39 – What It Means to Bootstrap a Business
03:33 – From Carpenter to Coach: The 31-Month Journey
06:13 – The Leap: Leaving Bob Proctor’s Team
08:19 – Launching One Sale a Day Club
09:13 – The “Road to 100” Whiteboard Visualization
11:05 – Building Momentum Through Monthly Events
12:02 – Pivoting to Digital During COVID
13:21 – Mastering Skills That Build a Million-Dollar Business
16:07 – Creating the First Course & Hiring the First Team Member
18:42 – The Core Lesson: Sales Drive Everything
20:02 – Become Obsessed with Serving Others
23:38 – FREE 21-Day Money Momentum Challenge
24:10 – Wrap Up & Conclusion
Listen & Subscribe:
Apple: https://podcasts.apple.com/ca/podcast/the-30-day-year-podcast/id1784321927
Spotify: https://open.spotify.com/show/62vRq5ODKWTj3ytW92zdiM?si=a7b78e0507bd40c3
YouTube: https://www.youtube.com/@conwaymentorship
Connect With Us:
Instagram → @conwaymentorship | @jacq_conway
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