From Secure Salary to Sleepless Nights: Gavin Kirkwood on Building a Business | Episode 47

Gavin Kirkwood didn’t fall into business ownership, he worked his way there. From starting out in call centres to becoming a top performer in national sales teams, Gavin built his career through consistency, resilience, and graft. After years working across fleet, rental, and asset finance for major organisations, he reached a familiar crossroads: stay comfortable, or back himself. In this episode of Success or Excuses, James Fleming sits down with Gavin Kirkwood, founder of Kirkwood Asset Finance, to explore what it really takes to launch and grow a business in a brutally competitive industry. Gavin shares why leaving a secure, high-performing role wasn’t an easy decision, how early deals didn’t land the way he expected, and what the last two and a half years of building from scratch have looked like. Gavin speaks openly about the pressure of running a young business, unpredictable cash flow, sleepless nights, and learning the difference between knowing an industry and being responsible for every outcome within it. From compliance and regulation to trust, pricing pressure, and long sales cycles, this conversation cuts through the polished version of entrepreneurship. James brings his own experience into the discussion, drawing parallels with building The Power Within Training, and sharing honest reflections on leadership pressure, hiring fears, systems, and responsibility. Together, they unpack resilience, trust, and why consistency matters more than comfort. Key moments include: ✔️ Starting out in call centres and building confidence in sales ✔️ Moving into fleet, rental, and asset finance ✔️ Becoming a top national performer in large organisations ✔️ The decision to leave security and start a business ✔️ Bottling it the first time, then backing himself ✔️ Early deals not landing as expected ✔️ Learning asset finance properly once the responsibility sat with him ✔️ Compliance, regulation, and commission disclosure changes ✔️ Speed vs price in asset finance decisions ✔️ Peaks, troughs, and unpredictable cash flow ✔️ Sleepless nights and pressure as a business owner ✔️ Why honesty and customer service win long-term ✔️ Losing deals you think are guaranteed ✔️ Reputation, trust, and working with larger clients ✔️ Sales culture, KPIs, and box-ticking ✔️ Hiring fears and protecting brand standards ✔️ Systems, processes, and CRM discipline ✔️ Gavin’s top three lessons in business and life Follow James Fleming: LinkedIn → https://www.linkedin.com/in/jamesflemingtpwtd/ Instagram → https://www.instagram.com/successorexcusespodcast YouTube → https://www.youtube.com/@SuccessorExcusesPodcast Website → https://thepowerwithintraining.com/ Follow Gavin Kirkwood: Website → https://www.kirkwoodassetfinance.co.uk LinkedIn → https://www.linkedin.com/in/gavin-kirkwood-43a46837/ Company LinkedIn → https://www.linkedin.com/company/kirkwood-asset-finance-limited/ Timestamps [00:00] James opens the episode and introduces Gavin Kirkwood [00:55] Gavin introduces himself and Kirkwood Asset Finance [01:20] What the business does and why customer service matters [03:16] Education, options, and challenging “we’ve always done it this way” [04:24] Why banks frustrate business owners [05:00] Tier one, two, and three funders explained [07:31] Speed vs price in asset finance [10:20] Early career in call centres and sales [11:00] Moving into fleet and commercial vehicles [13:59] Wanting more and outgrowing employment [14:18] Bottling the decision to go solo [14:47] Pressing the button and starting the business [15:22] Expecting early deals that didn’t arrive [16:16] Learning asset finance the hard way [17:22] Grit, persistence, and building from zero [19:23] Growth through referrals and reputation [20:17] Trust, service, and honest communication [21:40] The brutal reality of asset finance sales [23:15] Losing deals you think are guaranteed [25:16] Reputation and credibility with big clients [27:30] Reviews, referrals, and organic growth [29:02] Consultative selling and building trust [31:00] Growth fears and hiring challenges [33:19] Systems, CRM, and protecting standards [35:09] Hiring experience vs potential [36:43] Culture, honesty, and autonomy [42:23] Strategy vs day-to-day survival [44:28] Peaks, troughs, and financial stress [45:36] Resilience and trusting the process [45:55] Gavin’s top three pieces of advice [48:00] James closes the episode