How to Build a Startup Team That Thinks for Itself | Trivelle Simpson

Send us Fan MailHow do you build a team that can operate without the founder constantly supervising every decision?In this episode, Peter Boolkah speaks with Trivelle Simpson, founder of The Drive Group, about startup leadership, early hiring decisions and creating an environment where capable people have room to think and act for themselves.Trivelle explains why he believes investors should evaluate the founder as carefully as the idea, how his first hire helped open an entirely new growth opportunity, and why entrepreneurially minded employees need genuine autonomy rather than constant micromanagement.Peter and Trivelle also explore the difficult balance between trusting people, maintaining standards and intervening when even a highly talented team member crosses a line.You’ll discover:Why investment alone cannot compensate for weak leadershipWhat founders should consider when making their earliest hiresTrivelle’s three leadership choices: train, tolerate or terminateHow contrasting personalities can uncover new growth opportunitiesWhy entrepreneurially minded employees need autonomyThe danger of promising ownership while managing through controlWhy talented individuals must never become bigger than the organisationHow working as someone else’s number two can improve a founder’s leadershipWhy leaders should set the direction without dictating every stepThis is a candid conversation about trust, autonomy, accountability and the founder’s transition from being the person with every answer to building a team capable of finding its own.Archive note: This conversation was recorded in 2023. References to contemporary events and the Drive 250 competition reflect that period.ABOUT TRIVELLE SIMPSONTrivelle Simpson is the founder of The Drive Group, a Canadian business consultancy working with business owners on strategy, organisational capability and cash flow.His career has included financial markets, corporate roles, startup operations, consulting, real estate and venture activity. In this conversation, he shares the leadership lessons he developed while building teams and working across different business environments.CONNECT WITH TRIVELLE SIMPSONWebsite: https://thedrivegroup.caLinkedIn: https://ca.linkedin.com/in/trivelle-simpson-0b9a99abCompany LinkedIn: https://www.linkedin.com/company/thedrivegroupinc/Instagram: https://www.instagram.com/thedrivegroupinc/CONNECT WITH PETER BOOLKAHWebsite: https://www.boolkah.comLinkedIn: https://www.linkedin.com/in/boolkahInstagram: https://www.instagram.com/pboolkah/Facebook: https://www.facebook.com/BoolkahX: https://twitter.com/boolkahABOUT PETER BOOLKAHPeter Boolkah is a business coach, author and speaker who has spent more than 20 years helping business owners build stronger, more valuable businesses that do not depend on them for everything.He is the creator of The Hamster Wheel Trap® and author of Your Business Sucks: Build a Business That Works Without Destroying Your Life.Peter works with founders and leadership teams on the issues that ultimately determine whether a business creates freedom or becomes another job: leadership, founder dependency, people, profit, execution, scaling, exit readiness and enterprise value.His approach is direct, practical and built around one simple question:Do you own the business, or does the business own you?Learn more at https://www.boolkah.com