Kristopher "Kris" Grey is the founder of Creatapult and a seasoned project management consultant with over two decades of experience helping contractors and growing businesses scale without operational chaos. A self-described "construction brat" who grew up inside his family's contracting company, Kris launched his entrepreneurial journey under pressure — just days after the birth of his first child — and turned that crisis into a mission to help business owners build the systems, dashboards, and accountability frameworks they need to protect margins, reduce risk, and lead with clarity through fractional project management leadership.
SHOW SUMMARY
In this episode, Jonathan Goldhill is joined by Kristopher Grey of Creatapult about how contractors and other organizations can scale without operational chaos. Kristopher shares his origin story of losing all family income three days after his first child was born, which shifted his view that entrepreneurship and having a “side” income can be less risky than relying on one W2 job. Drawing on his upbringing in a family construction business, he describes common contractor failures such as bad bookkeeping, overreliance on tribal knowledge and heroics, understaffing project management, and the “death spiral” where winning more work leads to schedule slips, quality decline, change-order losses, and margin erosion. They discuss the “Who does what by when” accountability tool, dashboards, backup PMs, and the rise of fractional project management leadership. Kristopher outlines a 90-day execution engine focused on project intake, portfolio stabilization with RAG reporting, and risk tracking, and shares a transit-operator turnaround that enabled growth and COVID resilience.
KEY TAKEAWAYS
- Winning more work can kill a company. Growth without systems creates a "death spiral" — slipping schedules, declining quality, and cash flow collapse, even when revenue is rising.
- Bad bookkeeping is the #1 contractor mistake. If you don't know your margins, you can't manage your business — you're running a personal ATM, not a company.
- Project managers lose effectiveness past 2 projects. Overloading PMs is a silent killer of profitability and client relationships.
- "Who Does What By When" is the foundation of execution. Without a clear owner, a clear task, and a hard deadline, everything drifts.
- Systems are the antidote to turnover. With employees switching jobs every ~4 years, institutional knowledge must be documented — not held in someone's head.
- Fractional project management lowers the barrier to scaling. Companies don't need a full-time executive to get enterprise-level PM leadership — they just need the right fractional fit.
- Don't be afraid to ask for help. Pride is the number one source of doom for family construction businesses.
- Risk tracking is almost always missing. Most contractors react to problems instead of forecasting and mitigating them early.
- A RAG dashboard (Red/Amber/Green) gives leadership real-time project visibility and frees CEOs from daily firefighting to focus on strategy.
QUOTES
- "It's kind of like a fish drowning in water. You'd think that winning more work would be a good thing… but if they've not been managing those projects well, they're bleeding out." — Chris Grey
- "If you don't put a deadline on something, your project is always at risk of falling behind by the longest single scheduling item you have."
- "Pride is probably the number one source of doom for a lot of these companies — the name is often on the building."
- "Most employees are essentially a statistic or a number for a company — they can be let go at any time."
- "Always have something on the side. If the thing takes off, run with it."
- "Growth alone doesn't create successful companies — but execution does." — Jonathan Goldhill (closing)
- "We were doing more with less — but less stress overall — because the PMs had the tools they needed to be successful."
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www.DisruptiveSuccessor.comWhat is Disruptive Successor Podcast?
The Disruptive Successor Show is a podcast for next-generation leaders in family businesses and entrepreneurs who want to disrupt the status quo to grow their business and take it to the next level.
We all know that what got us here isn’t going to get us there.
If you are taking control over your family’s business or trying to get your business to the next level, you will need inspiration, advice and resources to help you create a massive impact.
Listeners of my show include not only the millennial or Gen Z but also the Baby Boomer and Gen Y. My listeners tend to be involved in these industries: business services, construction, design-build-maintain landscape contracting, food manufacturing, property management, real estate, and technology.
And are interested in issues like business coaching, branding, communication, difficult conversations, disruption, employee ownership, exit planning, financial management, leadership, innovation, intergenerational transfer, marketing, multi-generational family businesses, business operations, process documentation, security, selling, storytelling, succession, visioning, wealth management,
My guests are entrepreneurs, family business advisors, multi-generational and Gen 2 family business leaders, heads of university family business programs, consultants, coaches and firms that serve those who are growth businesses.
Clients of my show typically are running businesses with 10 to 200 employees and $1M to $20M in revenues.
Their concerns include: scaling up, exit planning, succession, leadership development, disruption, business planning, finances, growth planning, transferring generational wealth, transferring control, ownership issues, and more.
The benefits listeners receive are introductions to experts and advisors around the issues of growing and exiting a business, whether it’s a family business or entrepreneurial venture. They get a feel for the challenges other business owners and leaders face and how they overcame them. They will hear stories from people and how they came to do their work and why.
My shows feature handpicked guests who engage with me in casual conversations lasting between 30 to 40 minutes. You can expect to be entertained, engaged and may even get takeaways like business tools or ideas for implementation in your business.
I’ve led entrepreneurial adventures in art, clothing, a holistic health lifestyle magazine and trade show, shoe manufacturing. I’ve also led several non-profit organizations. I earned an MBA from the University of Southern California in Entrepreneurship.
I’ve been advising, coaching and consulting family-owned, family-run and entrepreneur-led businesses since 1989. My love for entrepreneurship follows the closure of my family’s sizeable multi-generational clothing manufacturing company after eight decades of operation because there were no successors.
After uncovering the code to scale up a family-run business - a playbook and a disruptive successor - I wrote a book called Disruptive Successor: A Guide To Driving Growth in Your Family Business.
My podcast is my effort to bring interested people into the conversation to benefit disruptive successors.