John Connolly - Make your growth story hold up in investor diligence

Episode #201: Cait Anderson — Building trust into a repeatable growth system

Trust breaks faster than funnels.
This episode is for operators trying to make growth predictable without killing speed.

Cait Anderson is Chief Marketing Officer at Winston Francois. In this conversation, she and Jason unpack what actually makes a growth system sustainable: predictable returns, clear operating rhythm, and trust that compounds instead of resets. They walk through concrete examples, including a B2B SaaS company spending $1M/month in paid media, how experimentation budgets are set at different stages, and why breaking a product promise can wipe out downstream revenue faster than any channel issue.

What you’ll hear

• How Cait defines a growth operating system across acquisition, nurture, and conversion
• Why early-stage teams need wide flexibility, while later-stage teams cap experimentation at ~10–20%
• A real example of reallocating spend that moved ROAS from 2:1 to 20:1—and why that was still not the end goal
• How broken trust (not missing features) kills retention, referrals, and revenue

Chapters

Timestamps from episode transcript

• 00:00 — Aspirational vs. functional promises and why trust breaks fast
• 01:14 — What a growth operating system actually is
• 02:50 — Compounding metrics, referrals, and overlooked revenue
• 04:16 — Early-stage vs. late-stage operating rhythm and spend mix
• 06:49 — $1M/month paid media example: foundation vs. experimentation
• 10:27 — Activation, funnels, and building demand before conversion
• 15:23 — Turning around a struggling ad program and rethinking ROAS
• 17:13 — North Star metrics, buyer intent, and what to track first

Links & resources

Guest
Cait Anderson — Chief Marketing Officer, Winston Francois
https://winstonfrancois.com

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Hank and Carly Schlissberg. Hank is the CEO of Evio Pharmacy Solutions, and Carly is a stay-at-home mom to their three daughters. Hank and Carly discuss their experiences as parents and entrepreneurs, sharing insights on managing time, setting priorities, and finding balance. They emphasize the importance of hiring exceptional people and prioritizing what truly makes a difference. Hank discusses how aligning incentives in the healthcare industry is key to growing and creating a sustainable, member-focused company.

Follow ⁠Winston Francois⁠ https://winstonfrancois.com/

LinkedIn - https://www.linkedin.com/company/winstonfrancois/

X - https://twitter.com/WFdoesgrowth

Instagram: - https://www.instagram.com/WFdoesgrowth

TikTok- https://www.tiktok.com/@WFdoesgrowth

Follow Jason Shafton:

LinkedIn - https://www.linkedin.com/in/jasonshafton

X - https://twitter.com/jasonshafton

Instagram - https://www.instagram.com/jasonshafton/

TikTok - https://www.tiktok.com/@jshafton

YouTube - www.youtube.com/@JasonShafton

Follow Alyssa Fox:

Instagram: https://www.instagram.com/afox19/

Evio:

https://www.evio.com/

X: https://x.com/EvioTeam

LinkedIn: https://www.linkedin.com/company/eviopharmacysolutions/

LinkedIn: https://www.linkedin.com/in/hank-schlissberg-17843/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Brian and Sam Rose, husband and wife duo and partners in Mvnifest, a single platform to manage your commerce operations, from concept to customer. Brian and Sam met in college and have been growing businesses and people together for nearly 20 years. They share their approach to parenting, business, and creating an environment of fun and generosity of spirit. They are no strangers to a late night and have created their own luck and success. Their mutual admiration, respect, and trust have fostered many successful businesses and three thriving kids.

Follow ⁠Winston Francois⁠ https://winstonfrancois.com/

LinkedIn - https://www.linkedin.com/company/winstonfrancois/

X - https://twitter.com/WFdoesgrowth

Instagram: - https://www.instagram.com/WFdoesgrowth

TikTok- https://www.tiktok.com/@WFdoesgrowth

Follow Jason Shafton:

LinkedIn - https://www.linkedin.com/in/jasonshafton

X - https://twitter.com/jasonshafton

Instagram - https://www.instagram.com/jasonshafton/

TikTok - https://www.tiktok.com/@jshafton

YouTube - https://www.youtube.com/@JasonShafton

Follow Alyssa Fox:

Instagram: https://www.instagram.com/afox19/

Mvnifest:

https://mvnifest.com/

Instagram: https://www.instagram.com/mvnifest/

X: https://x.com/sorryrobots

LinkedIn: https://www.linkedin.com/in/brian-rose-endless https://www.linkedin.com/in/samanthatrose/ https://www.linkedin.com/company/mvnifest/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Jessica and Marshall Morris, husband and wife duo and partners in HomeLife brands. They discuss the importance of relationships in business and parenting and the need to understand and support individuality. They also share their approach to parenting, which involves following their children's passions and providing guidance without stifling their creativity and independence. Jessica and Marshall Morris also share their resilience journey and how they have built businesses with impact that focus on saving animals and helping veterans.

Follow ⁠Winston Francois⁠ https://winstonfrancois.com/

LinkedIn -https://www.linkedin.com/company/winstonfrancois/

X - https://twitter.com/WFdoesgrowth

Instagram: - https://www.instagram.com/WFdoesgrowth

TikTok- https://www.tiktok.com/@WFdoesgrowth

Follow Jason Shafton:

LinkedIn - https://www.linkedin.com/in/jasonshafton

X - https://twitter.com/jasonshafton

Instagram - https://www.instagram.com/jasonshafton/

TikTok - https://www.tiktok.com/@jshafton

YouTube - www.youtube.com/@JasonShafton

Follow Alyssa Fox:

Instagram: https://www.instagram.com/afox19/

HomeLife Brands:

https://homelifemedia.com/

Instagram: @marshallsmorris @Jessicamariemorris

LinkedIn: https://www.linkedin.com/in/marshallsmorris/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this special Father’s Day episode, Jason flies solo and interviews Nick Aubin, the co-founder and CEO of Commons Clinic, about his experience as a dad and an entrepreneur. They discuss the challenges of balancing work and family life, the importance of being present and proactive as a parent, and the joy of watching their children grow and succeed. Nick shares his insights on the healthcare industry and the mission of Commons Clinic to provide accessible and affordable care. The conversation is filled with humor, honesty, and valuable advice for dads navigating the complexities of fatherhood and entrepreneurship.

Mentions and recommendations:

Ikigai

Yoto

Tonies

Nanit

Follow Winston Francois: LinkedIn - https://www.linkedin.com/company/winstonfrancois/ Twitter/X - https://twitter.com/WFdoesgrowth Instagram: - https://www.instagram.com/WFdoesgrowth TikTok- https://www.tiktok.com/@WFdoesgrowth Follow Jason Shafton: LinkedIn - https://www.linkedin.com/in/jasonshafton X - https://twitter.com/jasonshafton Instagram - https://www.instagram.com/jasonshafton/ TikTok - https://www.tiktok.com/@jshafton YouTube - www.youtube.com/@JasonShafton Commons Clinic: https://commonsclinic.com/ LinkedIn: https://www.linkedin.com/in/nick-aubin-56883647/ LinkedIn: https://www.linkedin.com/company/commons-clinic/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they engage in a fascinating conversation with Robbie and Emily Bent, the visionary co-founders of Othership. Othership is not just a platform, it's a transformative concept that combines a physical space and a mobile app. It's a solution to the pervasive issue of loneliness, offering a path to improved individual and collective health. Othership's unique approach fosters a sense of awe, belonging, and interconnectivity, enriching the human experience and leading to a more fulfilling life.

The conversation covers entrepreneurship, parenting, work-life balance, and personal growth. It delves into the challenges and rewards of building a business, the journey of becoming a parent, and the evolving definition of success.

Follow Winston Francois: LinkedIn - https://www.linkedin.com/company/winstonfrancois/ Twitter/X - https://twitter.com/WFdoesgrowth Instagram: - https://www.instagram.com/WFdoesgrowth TikTok- https://www.tiktok.com/@WFdoesgrowth Follow Jason Shafton: LinkedIn - https://www.linkedin.com/in/jasonshafton X - https://twitter.com/jasonshafton Instagram - https://www.instagram.com/jasonshafton/ TikTok - https://www.tiktok.com/@jshafton YouTube - www.youtube.com/@JasonShafton Follow Alyssa Fox: Instagram: https://www.instagram.com/afox19/ Follow Othership: Instagram: https://www.instagram.com/othership/ Instagram: https://www.instagram.com/othership.app/ TikTok: https://www.tiktok.com/@othership LinkedIn: Emily Bent - https://www.linkedin.com/in/emily-bent-2504082a/ LinkedIn: Robbie Bent - https://www.linkedin.com/in/robbiebent/ X - https://twitter.com/robbiebent1

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox delve deep into the complexities of business and personal growth. In episode one, Jason and Alyssa open up about the intricacies of balancing work, life, and parenthood. They talk about some of the advice they have gotten that was “total bullshit,” and share the unique and creative way they decided to celebrate the birth of their second child. It may have involved a 20-person shoot, and burgers being thrown in people’s faces. Watch Motherhood is Hot! Youtube @WinstonFrancois.