CEO School

UNLOCK Financial FREEDOM & Stop Wasting Your TIME

February 23, 2026

Key Takeaways Copied to clipboard!

  • True time management is prioritizing freedom of time over freedom of money, achieved by focusing only on "thousand-dollar tasks" and ruthlessly applying the "do, delegate, delete" method. 
  • Founders must define their end goal first to effectively reverse-engineer progress, focusing daily on only the three most important "needle-moving" tasks that align with that vision. 
  • Navigating systemic barriers as a female founder requires building a strong network, actively seeking allies, asking for help, and having the courage to show up authentically despite external doubt or exclusion. 
  • Scaling a business requires constant recalibration across people, process, and profit, as systems and structures are expected to break at each stage of growth. 
  • Core company values and culture must remain grounded and consistent as the business scales, serving as the DNA that carries the team through transitions and hard decisions. 
  • True fulfillment after achieving massive financial success often requires redefining success around freedom of time and impact, rather than solely chasing the next revenue milestone. 

Segments

Goal Setting and Reverse Engineering
Copied to clipboard!
(00:00:00)
  • Key Takeaway: Defining the end goal first is crucial for reverse-engineering real progress toward company or personal objectives.
  • Summary: Success requires knowing the destination before starting the journey. The rule of three helps prioritize the three most important tasks that move one toward the defined goals. Everything else should be considered for deletion or delegation.
Time Hacking and Productivity
Copied to clipboard!
(00:00:43)
  • Key Takeaway: Productivity for CEOs and working mothers hinges on being mindful of time as the most precious commodity.
  • Summary: The speaker identifies as a highly caffeinated time hacker due to the demands of being a CEO and mother of two young daughters. Time management evolved from chasing financial freedom to prioritizing freedom of time to enjoy the journey. Tasks must be evaluated as either high-value (“thousand-dollar tasks”) or low-value ("$10 tasks").
Do, Delegate, Delete Audit
Copied to clipboard!
(00:03:32)
  • Key Takeaway: Regular time audits are necessary to ensure time allocation aligns with intentional goals, using the ‘do, delegate, delete’ framework.
  • Summary: The speaker conducts a time audit every few weeks because life seasons change, requiring reassessment of time usage. This process helps identify habits that need to be delegated or deleted from the schedule. The job of a CEO is primarily helping everyone prioritize needle-moving work, acting as the coxswain in a boat rather than the rower.
Mindset Shift on Time
Copied to clipboard!
(00:04:08)
  • Key Takeaway: Believing one ‘has all the time in the world’ is achieved through presence and intention, shifting the experience from ‘busy’ to ‘intentionally full’.
  • Summary: The speaker overcame the mantra of having ‘all the time in the world’ without believing it by practicing presence in every activity. The world is fast-paced and on-demand, leading everyone to feel busy. The key shift is moving from being busy to being intentionally full with purpose.
Deciding What to Keep/Delegate
Copied to clipboard!
(00:05:33)
  • Key Takeaway: Prioritization criteria for the ‘do, delegate, delete’ method are rooted in the defined end goal, making everything else a ’no’.
  • Summary: Founders often feel they must do everything, especially without a team, but prioritization starts with knowing the destination. The rule of three applies to setting quarterly or yearly goals, and anything not directly supporting those three goals should be deleted. A CEO’s role is to ensure the team rows in the same direction by clarifying priorities.
Origin Story and Early Confidence
Copied to clipboard!
(00:08:54)
  • Key Takeaway: Early, consistent parental affirmation (‘You have it’) built foundational confidence that shielded the speaker from later workplace gender bias.
  • Summary: The speaker, a first-generation college graduate from immigrant parents, grew up feeling empowered and never noticed gender bias until entering the workforce. In corporate roles, she observed women only in support or admin positions, which was the first time she felt ‘different.’ Her father encouraged her to start her company after male bosses dismissed her idea, giving her six months to try before returning to an MBA.
Risk Assessment and Social Media Pressure
Copied to clipboard!
(00:19:35)
  • Key Takeaway: Risk assessment should focus on ‘what is the risk in not doing it’ rather than the risk of taking action, especially during prime earning years.
  • Summary: The speaker advocates for taking calculated risks during one’s prime, referencing the book ‘Die with Zero.’ She notes that social media over-saturates success stories while hiding failures, leading founders to set debilitating goals. Early goals should be purpose-driven (e.g., ‘get one ‘yes’ today’) rather than numerical targets, as execution, not just ideas, defines entrepreneurship.
Navigating the Boys’ Club
Copied to clipboard!
(00:29:46)
  • Key Takeaway: Female founders must proactively build networks, seek male allies, ask for help, and show up authentically to navigate male-dominated industries.
  • Summary: The ‘boys’ club’ operates through established relationships, necessitating that women actively build their own networks by getting ‘into the room.’ Women must overcome the tendency to carry all the burden and become comfortable asking for help from allies. The third key is to ‘do it anyway,’ showing up as oneself, even when facing sexism or ageism, and inviting co-created conversations for change.
Family Business Dynamics
Copied to clipboard!
(00:40:16)
  • Key Takeaway: Building a business with family requires clear role division, equitable value assessment, and proactive communication, ideally supported by a third-party coach.
  • Summary: Partnerships with family or friends often break down over money, emphasizing that business is inherently personal and requires nurturing like any relationship. The speaker and her brother maintained success by staying in their distinct lanes (brand vs. sales/operations) and ensuring equitable value perception. They utilized a ‘business therapist’ to address resentment proactively, treating the partnership as a relationship needing maintenance.
Unsexy Business Opportunities
Copied to clipboard!
(00:49:00)
  • Key Takeaway: Massive scaling opportunities often exist in ‘unsexy,’ behind-the-scenes B2B or infrastructure problems that are overlooked by those focused only on viral consumer brands.
  • Summary: The pressure to build a viral, consumer-facing brand for social media validation causes many to miss complex, high-value problems. The speaker’s billion-dollar success came from bridging a gap between card-present and card-not-present technology for businesses needing both. Execution, not just the idea, is what creates massive success, requiring consistent hard work every day.
Scaling Mindset Shifts
Copied to clipboard!
(00:54:03)
  • Key Takeaway: Achieving higher revenue milestones (e.g., $1M to $100M to $1B) demands a complete shift in mindset and the type of work required at each level.
  • Summary: The journey from zero to six figures, six to seven, and seven to eight figures involves distinct challenges where the existing structure is expected to break. Founders must up-level their approach at each stage to progress. The secret to billion-dollar success was simply refusing to give up despite near-failures like missing payroll or losing customers.
Scaling Mindset Shifts
Copied to clipboard!
(00:53:41)
  • Key Takeaway: Everything breaks at every stage of scaling, requiring a complete shift in mindset and work type to progress from one revenue level to the next.
  • Summary: Progressing from zero to six figures, six to seven, and seven to eight figures involves predictable breakage of systems and people due to increased pressure. Scaling requires leveling up mentality, new technology, and focusing on the three pillars: people, process, and profit. Companies achieving high valuations often shift strategy, such as moving from acquiring small businesses to an enterprise focus.
Culture and Values Consistency
Copied to clipboard!
(00:56:10)
  • Key Takeaway: Core company values and the DNA of the culture must remain grounded and consistent throughout scaling to ensure the right people are hired and retained.
  • Summary: The speaker intentionally worked hard to be the best leader possible, guided by the company’s unchanging value system. Decisions on hiring and firing are hard but must align with the core culture, exemplified by the ‘one team’ value tattooed on the speaker. These core values evolve but must stay grounded as the playbook changes for the next level of growth.
Post-Billion Valuation Emptiness
Copied to clipboard!
(01:00:24)
  • Key Takeaway: The toughest days can occur after achieving a major financial goal, leading to emptiness when the external goal is met but internal intention is missing.
  • Summary: The speaker experienced the worst health and felt the loneliest after achieving the billion-dollar valuation exit because they were chasing an undefined next goal (IPO/2 billion). This realization prompted a sabbatical to redefine personal goals, leading to the decision to step away from the CEO role to prioritize self and impact over equity.
Redefining Success and Health
Copied to clipboard!
(01:06:11)
  • Key Takeaway: The focus shifted from freedom of dollar to freedom of impact, allowing for intentional building with confidence and a focus on personal well-being.
  • Summary: The speaker is now building ‘Scenario 2.0’ without the pressure of dollar valuation, focusing instead on impact and personal fulfillment. Significant work was put into health, which is now incredible, and spiritual practices that were previously lost due to overwork. Growth requires checking ego and ensuring one’s actions align with stated values.
Balancing Family and Work
Copied to clipboard!
(01:10:32)
  • Key Takeaway: Maintaining a strong partnership and family life while building a massive company requires intentional integration, transparency, and prioritizing couple time over perfect balance.
  • Summary: The speaker credits their supportive partner and strong male role models for empowering their success, noting that strong men are needed for strong women. They utilize a weekly ‘Sunday Zoom Out’ meeting involving the children to ensure transparency and integration of schedules, rejecting the myth of perfect balance in favor of integration. Deprioritizing the relationship leads to negative consequences, making dedicated one-on-one time critical.
Final Five Insights
Copied to clipboard!
(01:19:03)
  • Key Takeaway: The ultimate freedom formula is achieving freedom of impact, preceded by financial security and freedom of time.
  • Summary: The best advice received is that everything is neither as good nor as bad as it seems, while the worst advice is underestimation or being told ’not now.’ The freedom formula is defined as freedom of dollar, freedom of time, and ultimately, freedom of impact. The world needs to be led with kindness, which should precede all actions and self-talk.