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Time is the most precious asset for any entrepreneur. In this powerhouse mastermind session, Josh Klenoff a seasoned entrepreneur, Wharton classmate of Elon Musk, and author of The System: How Companies Get Their Sh*t Together unpacks how to buy back your time, build leverage in your business, and create lasting freedom. Whether you’re a solopreneur drowning in tasks or a growing agency stuck in survival mode, this session offers a strategic blueprint to break free.
From Firefighter to Visionary: The Mindset Shift Every Founder Must Make
“Your most important role as an entrepreneur is creating openings.” – Josh Klenoff
Josh starts by highlighting the most dangerous trap for entrepreneurs: staying stuck in the weeds. Whether it’s putting out fires, responding to emails, or micromanaging your team, you’re limiting your growth if you’re spending your day doing tasks someone else could do for $20/hour.
The transition from practitioner to entrepreneur requires:
- Understanding your hourly value
- Calculating what you’re willing to pay to offload low-impact tasks
- Ruthlessly eliminating time waste
“I hated wasting time so much that it drove me to delegate.”
If you want to grow, you need to obsess over your time like a CFO obsesses over profit margins.
The Real Reason You Haven’t Delegated (And How to Fix It)
Most agency owners already know they should delegate. So why don’t they?
Common reasons Josh uncovers:
- Lack of trust due to previous bad hires
- Fear of losing client relationships or quality control
- Limited funds to hire true “A-players”
- Emotional attachment to tasks that feel comfortable
Josh shares a powerful mindset reframing: delegation isn’t about handing off tasks, it’s about elevating your role.
He also suggests a simple but effective tactic: design small simulations or scenario tests as part of your hiring process. This helps you spot red flags before someone starts.
“Don’t wait for the perfect person to appear. Create a clear job role, post it, and vet hard. Be relentless about your standards.”
Win-Win Hiring: Creative Compensation Structures for Growth
Hiring doesn’t always require a hefty payroll. Josh breaks down creative ways to attract talent when funds are tight:
- Hire That Company so you can enjoy a variable cost as you have clients/needs instead of an ongoing fixed salary cost. We help you sell and service your customers so you can focus on high leverage activities / growth.
- Performance-based roles: Only pay when a project is completed.
- Deferred compensation: Share revenue once the client pays.
- Co-created roles: Design the job with the hire collaboratively.
This is especially useful for:
- Strategists
- Operations help
- Specialized VA roles
“Everyone is a salesperson. Entrepreneurs get paid when the client pays. Create openings others want to fill.”
Avoid commission-only sales roles unless you’re hiring a unicorn. But for non-sales roles, deferred comp can be a powerful incentive when paired with purpose-driven culture.
High-Probability Sales: How to Sell Without Hating It
One attendee shared their struggle with cold calling and sales. Josh’s advice was simple but strategic:
- Stop scatter-gunning your outreach
- Adopt high-probability selling: Identify your niche, build conviction in your offer, and personalize outreach
- Eat the frog: Schedule the hard sales work first thing daily
“Sincerity is your secret weapon. Prospects can hear your motive. So come prepared with value, not a script.”
He recommends using multi-channel approaches (LinkedIn, email, phone) and tailoring each message so the prospect feels seen.
VA Hiring Benchmarks: What You Can Expect to Pay
In the final segment, Josh shares current benchmarks for hiring solid virtual assistants:
- $11-12/hour: Possible with 6 weeks of intense vetting
- $13-15/hour: More realistic for finding true A-players
He stresses that price is only one variable. Quality, initiative, and attention to detail should outweigh small cost differences.
“If you give yourself time to search well, the right person can change your life.”
Josh’s agency regularly finds VAs that become indispensable team members flying to client conferences, managing ops, and reducing burnout.
Final Thoughts: Freedom Comes From Letting Go
Josh Klenoff’s message is clear: you can’t scale if you’re clinging to control. Delegation isn’t a cost it’s a multiplier. If you value freedom, growth, and impact, it starts by buying back your time.
At That Company, we believe in building real freedom for agency owners. Our white label team handles your fulfillment, account management, and reporting under your brand.
Need help finding and onboarding your first assistant? Want help scaling operations without selling your soul?
Contact us today or subscribe to our YouTube channel to catch the next mastermind.
“He who takes risk drinks the champagne.”
