Two-time founder behind Rezdy and Budgetly reveals why building his second startup wasn’t easier and the harsh lessons every entrepreneur needs.
Why this matters: As Australia’s startup ecosystem continues to grow, second-time founders like Lenoir offer crucial insights into the persistent challenges that plague even experienced entrepreneurs, from cash flow management to the dangers of perfectionism.
When Simon Lenoir decided to start his second business in 2019, he carried with him the confidence of someone who had already conquered the startup world.
His first company, Rezdy, had grown from a personal frustration into a global booking platform used across more than 100 countries. Surely, he thought, lightning could strike twice with less turbulence.
“Building a business is not easy, even if you have done it before,” Lenoir admits, reflecting on his journey from scuba instructor to serial entrepreneur.
The story began in 2011 in the warm waters of Thailand, where Lenoir worked as a diving instructor but found himself drowning in administrative tasks instead of exploring coral reefs.
“The idea for the business was born from my frustrations while working as a scuba instructor in Thailand, where I found myself spending more time managing schedules and payments rather than diving,” he explains.
That frustration birthed Rezdy, and within years, Lenoir and his co-founder had built something remarkable. But after nine years of day-to-day operations, Lenoir stepped back into a non-executive role, ready for his next challenge.
Personal pain points drive innovation
Enter Budgetly, a spend management platform for SMEs that emerged from another deeply personal frustration. As Rezdy grew, Lenoir watched his team submit credit card statements at month’s end, revealing overspending and missing receipts that turned financial reconciliation into detective work.
“Trying to reconcile the budget and the receipts every month started to feel like a never-ending game of forensic accounting,” he recalls.
This experience reinforced a crucial lesson that spans both his ventures: authentic innovation stems from genuine pain points.
“At Rezdy, the pain point was personal. I’d lived the chaos of running a dive shop and knew and related to the challenges of double bookings and no-shows, which fuelled my passion for the product and helped gain credibility with customers,” Lenoir says.
With Budgetly, now operating with over 30 employees, the pattern repeated. “Having experienced that problem firsthand and then building a product to elevate it is something I’m incredibly proud and passionate about, and passion in business is infectious.”
Cash flow reality check
The transition from first-time to serial founder brought hard-earned wisdom about financial discipline. In his early Rezdy days, Lenoir admits he “focused on growth at all costs” but learned the hard way that sustainable expansion requires careful cash management.
“Cash flow is king,” he states emphatically, describing how Budgetly takes a fundamentally different approach from day one.
The company uses its own platform internally to track every payment and set departmental budgets, while integrating with Xero to monitor incoming payments. “Having the ability to see our cash flow position in real-time allows for fewer surprises and helps us make faster, more strategic decisions.”
Embracing imperfection
Perhaps the most counterintuitive lesson from Lenoir’s second act involves abandoning the pursuit of perfect systems. At Rezdy, he spent months customising CRMs, finance tools, and analytics dashboards, believing the company needed the “right” system before moving quickly.
“This time, we utilise lightweight tools, off-the-shelf integrations, and automate early, which helps us accelerate our time to market. They may not be 100% perfect but they help us get where we need to be,” he explains.
The philosophy extends beyond technology. “Startups don’t die from imperfect systems. They die from indecision, slow execution, and wasted time.”
Leadership through delegation
The most personal evolution in Lenoir’s approach involves recognising the limits of hands-on leadership. As a first-time founder, he inserted himself into every business aspect, joining sales calls, handling customer support, and building product wireframes.
“However, I quickly learned that you can’t lead a business, a team or a vision if you burn out from trying to ‘do it all’,” he reflects.
At Budgetly, he’s embraced a different model, trusting his team of experts to handle their specialised roles. “As a founder, your job is not to do more or do it all. It’s to concentrate on the things that matter. Delegating tasks and then getting out of the way to let your expert employees handle the details is where true leadership lies.”
The AI advantage
One significant change between Lenoir’s first and second ventures involves the democratisation of artificial intelligence. When he launched Rezdy in 2011, AI was “predominantly only accessible to larger organisations with bigger budgets.”
Today, Budgetly leverages AI internally to summarise meetings, prototype UI, and analyse data. “It replaces dozens of hours a week, giving us back time to focus on making those impactful business decisions that move the needle.”
From a hiring perspective, AI supports junior administrative and data entry tasks, allowing the company to “streamline our administrative roles and invest more in senior talent.”
Wisdom for the journey
Despite his accumulated experience, Lenoir acknowledges that running a business remains challenging, regardless of how many times you’ve done it. His advice focuses on sustainable progress rather than dramatic breakthroughs.
“Small steps make a big difference,” he says. “As a founder, we’re not going to get it right every time, but being willing to move forward, take the lessons and accept that we’re always learning helps.”
The mindset shift from his first venture to his second is significant. “I’m much more practical, focused and forgiving the second time around,” he notes.
For fellow SME owners feeling the friction of business operations, Lenoir offers reassurance grounded in experience. “All problems are solvable and many are temporary. Move fast, spend wisely and above all else, know that you’ve got this.”
Simon Lenoir is the founder and CEO of Budgetly, a spend management platform for SMEs, and founder of Rezdy, which was sold to a US private equity firm in 2023. Follow more founder insights in our Founder Friday series.
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