Second Time's Different: Randy Herbertson on Building The Visual Brand After Selling His First Agency

Scott Ward, host of the HabitStack Podcast, interviews Randy Herbertson, president of The Visual Brand (TVB), a branding studio based in Westport, Connecticut. Randy shares his journey from building his first agency to 40 people in New York City, selling it to a media company (which he warns against), and leaving after six miserable months when the promised synergies turned into constant trouble. He explains the key lessons from starting his second studio: ditching the three-hour NYC commute, avoiding web development he couldn't manage, and staying intentionally smaller at 20 people to remain hands-on with creative work. The conversation explores Randy's decision to turn down multiple acquisition offers despite tempting numbers, the critical importance of having a supportive life partner during pivots, and why he believes twists and turns lead to good places if you maintain a positive attitude. They discuss right-sizing teams to balance capacity without burnout, the challenge of letting go of toxic employees too late, and why daily standups transformed team organization. Randy reveals TVB's two specialties that set them apart: motion communications (2D/3D animation that's still a human practice despite AI) and packaging design (a surprisingly specialized field where most agencies fail at execution). He also shares why Studio feels more creative than Agency, and how maintaining work-life boundaries like clearing emails before leaving keeps Monday mornings exciting rather than dreaded.