Scaling Up Insights: Pandemic pivots, purpose, and company culture with three coaches

Executive overview

Recorded in October 2020 during the pandemic's second wave, this coach panel explores how entrepreneurs are adapting their businesses, rethinking the office, and reassessing personal purpose. Hosts Bill Gallagher, Cheryl Beth Kuchler, Cheryl Biron, and Matt Kazam share client stories and their own pivots — from free coaching to virtual comedy shows — to illustrate what it takes to stay relevant in disruption. The conversation covers co-founder dynamics, core values, remote work trade-offs, responsible wealth, and the mental-health case for workplace humour. The central lesson is that the leaders who stop waiting to return to "normal" and instead build for the world as it is now will be the ones who come out stronger.

Pivoting through the pandemic

• Coaches who gave away services early in lockdown paradoxically attracted more clients and stayed busier than before.
• Matt Kazam shifted from live corporate entertainment to virtual comedy workshops; free trial programmes became paid product lines.
• Cheryl Biron pivoted a trucking company during the Great Recession by shedding fixed assets and automating back-office work — a template she now applies to client advising in COVID.
• Commercial real estate operators who acknowledge tenants will not return are reinventing as "virtual landlords," providing remote-work infrastructure instead of floor space.
• Greg Crabtree observed more entrepreneur innovation in six months of pandemic than in the prior five years; constraints force creative problem-solving.
• Airbnb grew through the crisis by doubling down on co-founder role clarity, daily huddles, and KPI discipline — not by reverting to old playbooks.
• Deb Gabor's framing — "How can we be indispensable right now?" — became a practical planning touchstone for multiple coaches on the panel.

The office, remote work, and the human cost

• Extroverts working from home without a plan are struggling; companies need to actively build remote culture, not just declare "work from home."
• Studio sheds and accessory dwelling units surged as people created dedicated home-office space, signalling lasting structural change to commercial real estate.
• Manufacturing and healthcare clients had no remote option; pandemic planning meant designing safe split shifts and physical distancing protocols, not Zoom calls.
• Many people who wanted remote work in the abstract were unprepared for the reality of children at home, no physical separation from family, and loss of social identity.
• Metrics and productivity tracking are coming for remote workers; freedom from commute does not mean freedom from accountability.
• In-person client retreats resumed outdoors with masks by September 2020; participants were visibly grateful for any face-to-face contact after months of isolation.
• Some cities are seeing population outflows to lower-cost areas, accelerating geographic redistribution of talent — an advantage for companies comfortable with fully distributed teams.

Co-founder dynamics and the integrator-visionary split

• Airbnb's co-founder structure illustrated a pattern familiar to Scaling Up coaches: a visionary, outward-facing CEO paired with an operationally focused integrator.
• Complementary strengths only work if compensation is unified, egos are subordinated, and roles are clearly delineated — otherwise partnership friction destroys execution.
• Darius Moshizadeh and his COO Ali are cited as a real-world example: Darius's top-heavy StrengthsFinder influence profile was balanced by Ali's analytical rigour.
• Matt notes most famous comedy duos privately disliked each other; the partnership works despite personal friction when mutual dependence is genuine.
• Cameron Herold's COO Alliance exists precisely because visionary CEOs are increasingly becoming public brands, leaving a gap that only a skilled operator can fill.
• Bad partnerships are more common than good ones; picking the right complementary partner is the first and most important decision.
• Retaining senior talent is easier when the COO or second seat is a real, valued role rather than a step below a single decision-maker.

Core values as a management operating system

• Darius Moshizadeh's book "The Core Value Equation" argues values must be rich and descriptive, not aspirational slogans — they should describe how the company behaves when doing things right.
• Values only function operationally when infused into hiring, rituals, daily decisions, and coaching conversations rather than posted on a wall.
• A COO drowning in questions should stop giving answers and start asking which company value applies, then coaching employees to self-resolve.
• Accountability assignment is a prerequisite: 75 people cannot use values as a decision framework if no one knows who owns what.
• Values-based hiring increases cultural fit and reduces the need for a thick policy manual; people fire themselves when their values conflict with the company's.
• Matt's "suite stand-up challenge" — where leadership teams perform five-minute comedy sets — is used as a lived demonstration of values around fun, vulnerability, and psychological safety.
• Values embedded as budget line items (e.g., giving 10% to a school in Haiti) are more credible than values expressed only in words.

Workplace humour as a wellness and retention tool

• Matt's corporate comedy work migrated from sales and leadership buckets to the wellness budget in 2020, reflecting employer anxiety about mental health during lockdown.
• Laughter is described as the most powerful low-cost culture intervention available, with immediate measurable effect from the moment it is reintroduced.
• Post-pandemic workforce reduction means companies will need to invest more in retaining and engaging the humans who remain — robots cannot provide belonging.
• Leadership permission is critical: a CEO who publicly does stand-up signals that humour and vulnerability are safe for everyone.
• Bill's own stand-up experience at Caroline's in New York — coached by Matt — unlocked a looser, more authentic presentation style that improved client feedback over time.
• Stand-up comedy training teaches joke structure, timing, and audience reading — transferable skills for executive communication and storytelling.
• The science of joke writing can be taught in a half-hour workshop; teams who co-write comedy together bond and engage in a way that conventional team-building rarely achieves.

Purpose, legacy, and giving while alive

• Verne Harnish's Insights highlighted Chuck Feeney, co-founder of Duty Free Shops, who gave away $8 billion before death, leaving himself only a comfortable living.
• Feeney's principle: give while you live so you can observe impact, iterate on it, and see the good you create — waiting until death wastes the feedback loop.
• Sam Simon (The Simpsons) similarly spent his terminal illness giving his entire fortune away; the panel sees this as a model for intentional wealth deployment.
• Younger consumers and employees will not spend money on or work for brands that lack a visible social mission — evolved enterprise is a competitive requirement, not optional PR.
• Bill references Lynn Twist's "Soul of Money": money is a neutral instrument that amplifies whatever values it flows through — the question is which values you choose.
• The One Page Personal Plan, reviewed between Christmas and New Year's, will be unusually charged in 2021 as executives reassess life priorities shaped by pandemic disruption.
• Embedding giving into operating budgets as a line item is more sustainable than end-of-life philanthropy.

Tools, resources, and upcoming programmes

• Growth Institute provides online deep-dive courses on all Scaling Up topics; the Master of Business Dynamics (MBD) programme functions as an entrepreneurial MBA.
• Align Today (Scaling Up Scoreboard) is the panel's preferred tool for managing quarterly priorities, OKRs, and dashboards — purpose-built for the Scaling Up framework and integrated with Slack and Zapier.
• Cheryl Biron's two-hour "Reimagine Your Business" webinar on 18 November 2020 is designed to help teams set strong 2021 plans.
• Cheryl Beth Kuchler's new six-month Scaling Up Foundation programme builds the core infrastructure for companies earlier in their growth journey.
• Matt Kazam's Laugh You Win programmes include virtual joke-writing workshops, a Thanksgiving family comedy show, and licensing for other facilitators to deliver humour-based workshops.
• Scaling Up coaches at scalingcoach.com span 200+ practitioners in varied styles; the network can match prospective clients to the right coach personality.
• Online Scaling Up workshops now attract participants from India, Hong Kong, New Zealand, and the Middle East — geographic reach that in-person events rarely achieved.

Navigating information overload and the second wave

• Doom scrolling is a recognised threat to mental health; several coaches deliberately limited news consumption and shifted to Financial Times, The Guardian, and The Economist for signal over noise.
• Confirmation bias drives social media consumption: people click, share, and follow content that reinforces existing fears and beliefs, deepening polarisation.
• Reading past the headline — a principle Twitter itself was promoting in late 2020 — is the minimum standard for staying informed without being manipulated.
• Second COVID waves were already arriving in Canada, the UK, and Europe during recording; the panel urged clients to plan for continued disruption, not a near-term return to normal.
• A vaccine rollout was seen as the next major uncertainty, with considerable scepticism about public adoption timelines and conspiracy resistance.
• The panel modelled a growth mindset: "never finished" — Bill's explicit personal value — is about finding liberation in permanent incompleteness rather than anxiety about not yet arriving.
• Personal anecdotes of grief (Jack Pollard's death) reminded the group that COVID risk is real and uneven, particularly for older people and those with underlying conditions.