What does it really take to leave the comfort of corporate life and chase a dream?

In this episode, Lauren Bailey sits down with Bob Perkins. He is the founder of the AA-ISP and a pioneer in inside sales.

Bob shares how he went from a corporate sales leader to building a national community and later reinventing himself through music.

He talks about starting a dream project while still working a full-time job. He opens up about knowing when it’s time to move on and how to stay inspired later in life.

You’ll hear the real side of retirement. The mix of pride and loss. The tug between letting go and staying connected.

Key Takeaways

Introduction (00:00) 

From teacher to sales leader (01:24) 

Building AA-ISP (03:27) 

Music and passion (07:31) 

From corporate to entrepreneur (10:37) 

Lessons from building a community (13:51) 

Knowing when to exit (18:39) 

Rediscovery and finding purpose in retirement (20:31) 

Legacy and lessons (28:24)

🎧 Tune in for a warm and honest chat about legacy, leadership, and following your heart long after the first act ends.

And check out the community behind this show: https://legacy.wearegirlsclub.com/podcast

Connect with our host on LinkedIn. 

Sometimes the hardest chapters of our lives become the foundation for everything that follows thereafter.

Lori Richardson has spent over 40 years breaking barriers in sales and leadership. She started as a teacher, jumped into technology sales when it was still a boys’ club, and eventually built her own successful company.

Along the way, she’s faced adversity, doubt, and moments that could’ve stopped her but became fuel for her success.

Lori opens up about her early life, including how watching her grandmother run a business taught her to stand tall and speak up. She also shares how surviving an abusive relationship pushed her to rebuild her life, one brave decision at a time.

🎧 Hit play to hear Lori’s raw, inspiring journey and the lessons she wants every woman and man in leadership to know.

Key Takeaways

Introduction to the episode and Lori Richardson (00:00)

Lori’s journey from teaching to technology sales (01:15)

When is the right time for leaders to transition to entrepreneurship? (03:20)

Why sales experience is invaluable in any career (05:18)

The importance of mentorship and sponsorship (07:44)

Lori’s early career mistake of not negotiating salary (08:01)

How early adversity fuels high performance later in life (10:32)

Overcoming fear and leaving a toxic relationship (13:28)

Lori’s vision for women in leadership and diversity in companies (15:55)

If you’re ready to be inspired by a leader who’s built her success through persistence, passion, and purpose, hit subscribe and tune in for Lori’s story and insights.

And check out the community behind this show: https://legacy.wearegirlsclub.com/podcast

Connect with our host on LinkedIn.

In this vulnerable and energizing episode of After the Title, LB sits down with Mark Kosoglow, CRO at Docebo and legendary sales leader from Outreach, to unpack how leaders can recognize when they’re out of alignment, and what to do about it.

Mark shares deeply personal and practical stories about his journey from founder back to CRO, the emotional signs that told him he wasn’t in the right place, and how to distinguish between "business dad" and "family dad," a metaphor that reveals when work stress is taking over your life.

You’ll learn why fun is the fuel for hard work, how great leaders coach through questions instead of solutions, and the three things Mark believes every executive must do to add value at the C-level.

We also talk about what true leadership looks like, building your squad, showing up for your people, and influencing behavior through trust.

Key Takeaways

Mark Kosoglow’s career journey and self-identity (0:01)

Challenges of founding and returning to revenue leadership (2:43)

Recognizing the right job and work-life balance (4:12)

Balancing business and personal life (15:16)

Developing self-awareness and emotional intelligence (15:30)

Transitioning from executive to C-level roles (15:59)

Building and leading a squad (18:24)

Mark's leadership philosophy and personal brand (26:58)

Mark's inner circle and legacy (27:14)

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Check out the community behind this show: https://legacy.wearegirlsclub.com/

Connect with our host on LinkedIn. 

In this episode of After the Title, LB sits down with Regina Manfredi, President at Software One, for a raw look at what really matters in executive leadership.

Regina opens up about the glass ceiling and the trade-offs women leaders still face, why she believes “culture will eat strategy for breakfast”, and the champagne-and-laughter legacy she hopes to leave behind.

Key Takeaways

Regina Manfredi's introduction and role (00:00)

Critical thinking and decision making in the workplace (01:39)

The importance of asking questions (03:36)

Cultural influence and core values (05:36)

The glass ceiling and personal sacrifices (08:16)

The power of fun and technology's impact (10:07)

Regina's promotion to president (11:45)

Final reflections and advice (15:08)

This is an honest, practical conversation on leadership development and career transitions at the executive level. 

And check out the community behind this show: https://legacy.wearegirlsclub.com/

Connect with our host on LinkedIn. 

Hosted by Lauren Bailey, Founder of Legacy Executive Club, this episode features Anna Baird, Operating Partner at Madrona and former CRO/COO/CFO who helped scale Outreach to unicorn status and was the global lead partner for Google at KPMG during its IPO years. With decades of Silicon Valley leadership across Intuit, McAfee, and more, Anna shares candid lessons for leaders who want to grow careers and companies.

Key Takeaways

2:20 – 3:18 Imposter syndrome never goes away, even at the top

6:23 – 7:26 Taking risks and fixing what’s broken: the art of the possible

8:28 – 9:52 The biggest career “train wrecks” and lessons learned

10:26 – 12:24 Why listening to customers, product, and employees is a leader’s superpower

14:09 – 16:14 The danger of manipulating data and the need for one source of truth

17:16 – 18:49 Spotting and repairing the “relationship gap” at the executive level

22:19 – 24:40 Legacy lessons: teaching, listening, and being remembered for impact

This is a masterclass in strategic listening, resilience, and building trust from someone who’s sat in nearly every C-level seat.

If you liked this episode, share it with a colleague or work friend who’s ready to lead differently.

And check out the community behind this show: https://legacy.wearegirlsclub.com/

Connect with our host on LinkedIn. 

Climbing the ladder is one thing. Learning what really matters on your way to the top is another.

After the Title is a podcast for high-achieving leaders, and those on their way, who want the truth about what leadership really looks like. Hosted by Lauren Bailey, these are unfiltered conversations with executives who’ve hit the top and started asking deeper questions:

What truly matters now?

Is anyone else dealing with this? 

What will I leave behind?

Each week, Lauren sits down with leaders to explore the stories, pivots, and defining moments that shaped their legacy — and the humans they became along the way.

If you’re craving purpose beyond performance, mentorship beyond metrics, and meaning beyond the title... you’re in the right place.