INSEAD

Megan Pillsbury Interview: Advise on Starting a Business

Megan Pillsbury shares candid advice for aspiring entrepreneurs, emphasizing that launching a venture is akin to a roller coaster—thrilling yet daunting. She frames the experience as pushing a cart uphill only to be dragged downhill, underscoring the emotional volatility inherent in startup life. Pillsbury stresses that the journey is stressful and best suited for those who thrive on uncertainty and crave freedom from rigid role definitions. She notes that many founders regret not trying rather than the act of trying, and highlights a pivotal four‑year horizon where businesses often face a make‑or‑break decision. Drawing from her own two‑startup trajectory, she recounts a first venture that lasted four years before she chose to exit, recognizing that genuine passion would have compelled her to persevere. She remarks, “I have never met a founder that regretted trying to start a business,” reinforcing the value of taking the leap. The interview serves as a rallying call for potential founders to act despite fear, prioritize timing, and ensure deep personal passion to sustain them through inevitable challenges, ultimately shaping a more resilient entrepreneurial ecosystem.