Proven Podcast: "From Single Mom to 2 Billion – How Class and Courage Win"

Guest: Dr. Ann Kaplan Mulholland
Host: Charles Schwartz
Date: January 14, 2026

Episode Overview

This episode of the Proven Podcast features Dr. Ann Kaplan Mulholland, who shares her extraordinary journey from being a single mother to building a $2 billion business empire. The conversation dives deep into the realities of entrepreneurship, leadership, personal branding, and navigating success as a woman. Ann discusses not only her financial achievements but her emphasis on values, authenticity, and the courage to think big. This episode is packed with tactical insights for entrepreneurs—especially women—on balancing life, career, and legacy.

Key Discussion Points and Insights

Who is Ann Kaplan Mulholland? (00:39–03:18)

• Ann primarily identifies as a mother, despite her entrepreneurial success:

  "I’d say I’m a mom... But there is no reason to be a business person as well." (00:58)

• Built a $2B finance business in unsecured loans, invested in real estate, and became a TV personality.
• Holds an MBA, MSc, Doctorate, and an interior design degree—demonstrates the blend of intellect, creativity, and drive.

Defining Success Beyond Finances (03:18–05:06)

• Ann and Charles highlight that true fulfillment comes from relationships and values, not just money.
• Ann shares the challenge of being perceived as “a wallet” as her wealth grows:

  "People look at me... they don’t see me, they see a wallet. It’s a rude awakening." (04:11)

• Stresses the importance of not basing identity on money.

Gender Bias and Navigating Stereotypes (05:35–07:57)

• Ann purposely separates her image from her businesses to prevent being targeted for her gender and wealth.
• Discusses the double standard in business, where being female and friendly is often mistaken as weakness or naivete.

  "Unfortunately, Charles, they mistake being female as being naive." (05:35)

• She establishes firm boundaries to avoid being exploited for investments.

Balancing Work, Life, and Family – The Tactical Side (07:57–10:16)

• Ann's routine as a single mom: disciplined mornings, delegating responsibilities to her kids, tightly managed schedules and budgets.
• Delegation began at home and translated into business:

  "When you have a number of kids, you have no choice but to train them." (07:57)

• Stresses the need to view both time and money as resources.

Delegation and Building Strong Teams (10:16–12:29)

• Ann hires for talent and values, then delegates accordingly:

  "I try to look for the talent that each individual has... And then delegate and trust." (10:16)

• Quick to remove those who are dishonest or disrupt positive culture.
• Trust and loyalty with management: encourages hiring people stronger than oneself, ensures managers aren’t threatened by talent.

Hiring and Management in a Changing World (12:29–15:52)

• The hiring process involves gut feel, value alignment, and careful HR vetting.
• Comments on challenges of work ethic post-Covid and the global skilled labor shortage.
• Importance of creating purposeful, fulfilling work environments—beyond financial compensation.

Fulfillment, Values, and Self-Awareness (15:52–21:08)

• Ann credits her "inner peace" and living by core values as her compass:

  "What you see [is] always what you get. I live from the core of values… that’s important." (15:52)

• She faced rejection—30 banks said no before one backed her.
• Real estate investing as a safety net; "annuity" mentality.
• Maintains modest personal spending habits despite great wealth.

Memorable Quote:

“Money wasn’t important to me, making money… But showing it off didn’t drive the Ferrari. I dressed in secondhand clothes. I still buy secondhand clothes.” (19:11)

Branding and Online Presence – Owning Your Identity (21:43–23:14)

• Brand management is critical, especially for women.
• Advice: "Clean up your act. If you really, really want to be something, and be that brand at all times." (19:27)
• Recognize the permanence of online actions and the importance of a calculated digital footprint.

Tactical Advice for Female Entrepreneurs (23:14–27:39)

• "Own who you are"—confidence is key.
• Outwork and outprepare everyone else in the room—do more research and anticipate all questions.
• "Think really, really big"—be ambitious, scalable, and adaptable.

  "There is no reason that you cannot be everything." (23:52)

• Incorporate AI and continue your education.
• No substitute for hard work; don't expect overnight success.

Notable Quote:

“No one became successful as an entrepreneur without putting the work in. You’ve got to roll your sleeves up.” (26:00)

Empowerment and Overcoming Comparison Traps (29:26–35:45)

• Women must stop comparing and threatening themselves; accept that "big thinking" may be intimidating but is necessary.
• Leverage organizations, committees, and creative networking to expand contacts.

  "Every moment is your elevator pitch. Take those elevator pitches and have that little sound bite available." (32:59)

• Use memorable, personal notes to maintain meaningful connections.
• Be noticeable in a positive, creative way at large events.

Networking Tactics for Women (38:10–41:47)

• Make and maintain notes about contacts, follow up authentically—never just to ask for something.
• Build networking events/communities for peer connection.
• Don’t mix personal life with professional branding; be intentional with group composition at professional events.

Dealing with Harassment and Professional Boundaries (41:47–47:44)

• Ann is direct about intent and boundaries:

  "First of all, you need to not be approachable. When something does happen, address it and be very professional..." (43:22)

• If harassment occurs, set clear, non-threatening boundaries and maintain professionalism.
• Don't let past mistakes define you; adjust and move forward with integrity.

Systems, Scaling, and Distribution in Business (47:44–51:50)

• Use “reverse engineering”: define big goals, then build backward to necessary systems and distribution channels.
• Whether B2B or B2C, understand your audience and serve their needs.
• Technology (websites, booking engines) is critical for scaling service businesses.

Building Teams and Incentivizing Talent (51:50–54:44)

• Bonuses based on company performance, not just individual metrics.
• Invest in employee education tied to business relevance.
• Don't offer equity; keep incentive structures straightforward.
• Key mantra: “Invest back in your employees—they are the biggest asset you have.” (54:09)

Real Estate, Investments, and the Future (54:45–64:16)

• Avoid residential real estate for now; focus on properties that can be rented, or warehouse space linked to new consumer behaviors.
• Be wary of investing in unfamiliar vehicles like crypto:

  “If you don’t understand it, you’re not investing, you’re gambling.” (64:16, quote relayed from Melvin Simon)

• Learning directly from experts is invaluable—seek multiple opinions before choosing a path.

Personal Branding & Breaking into Online Fame (65:33–71:12)

• Emphasizes the importance of controlling your image across platforms.
• Model yourself after admired brands (e.g., Richard Branson) and own your story.
• Keep personal matters private to protect both family and brand.

How to Connect with Ann Kaplan (71:12–72:00)

• Message on Instagram: @AnnKaplan (A N N K A P L A N)
• Mention the podcast for a response, as messages are screened by her team.

  “Reference your podcast... That will get more attention because behind the scenes, I have someone else who manages my messages.” (71:12)

Memorable Quotes & Moments (with Timestamps)

• On Identity:

  "If at the end of the day, if I was a good mother, I would be proud and a good daughter and a good friend, I would be proud. So I’m a mom. But… there’s so many more aspects of who we are." (02:51)

• On Success:

  "The people that were the happiest… always started with, 'I’m a mom…' or 'I’m a husband…' But what really matters at the end of the day is who you are and what fills your heart." (03:18)

• On Delegation:

  "I only have so much energy and so much time in the day. I need to view my time as a resource as much as I view my finances as a resource." (09:25)

• On Building Networks:

  "Join committees and organizations in a large scale and you will meet more people... Open your world." (31:50)

• On Being a Woman in Business:

  "Own who you are… you don’t have to fit into some profile. Gone are the black suits and the white shirts and having to dress like men. Be who you are." (23:24)

• On Success Mindset:

  "No one became successful as an entrepreneur without putting the work in… be adaptable to change, and females are more adaptable." (26:00)

• On Risk:

  "If you don’t understand it, you’re not investing, you’re gambling." (64:16)

Notable Segments

• [00:58]–[03:18] Introduction and Ann’s background
• [05:35]–[07:57] Navigating gender bias and being seen as a wallet
• [10:16]–[12:29] Delegation, hiring, and team culture
• [15:52]–[21:08] Finding fulfillment, values, and financial persistence
• [23:14]–[27:39] Tactical advice for women: Own it, think big, AI education
• [29:26]–[35:45] Empowering women to think bigger, expanding your network
• [38:10]–[41:47] Building, maintaining, and creating your own networking events
• [41:47]–[47:44] Dealing with inappropriate advances and setting boundaries
• [47:44]–[51:50] Systems, scaling, and establishing distribution
• [51:50]–[54:44] Incentivizing and growing talent
• [54:45]–[64:16] Market analysis: Real estate, crypto, investment strategies
• [65:33]–[71:12] Social media, personal branding, and breaking into online fame
• [71:12]–[72:00] How to connect with Ann

Final Takeaways

• Authenticity and values are the foundation of lasting success.
• Own your identity, both in person and online—your brand is your most powerful tool.
• For women: Outprepare, outwork, and outthink—don’t shrink to fit norms, and don’t be afraid to think and act bigger.
• Success comes from resilience, adaptability, and smart delegation—not overnight, but through relentless intentionality.
• Be strategic and cautious with investments; don’t gamble on what you don’t understand.
• Network proactively and with integrity—be in service to others, and build relationships, not transactions.

Connect with Ann:
Instagram: @AnnKaplan (mention this podcast episode)

“How you live online is how you get paid offline. If you don’t control your image, someone else will.” — Charles Schwartz, [72:41]