What Coaching Is
A partner who helps
you build the plan
and stick to it.
Business coaching with Jon is not motivational speaking or generic advice. It is a structured, ongoing working relationship built around your specific goals, your specific business, and your specific obstacles.
Jon guides clients through the process of getting clear on where they want to go, identifying what's actually in the way, building a realistic plan to get there, and staying accountable to executing it. The difference from most coaches: Jon has held VP, Director, and CFO-level roles, so the plans he helps you build are grounded in what actually works in real organizations.
Coaching engagements are highly personalized. Sessions can be weekly, bi-weekly, or structured around project milestones — whatever rhythm drives the most momentum for you.
Schedule a Free Discovery Call
"The objective of the coach is to enable growth by capitalizing on strengths and augmenting weaknesses."
— Jon Rickards, Coaching Philosophy
What We Work On
Every dimension
of your business growth.
Coaching sessions with Jon can address any area where clarity and a plan would move your business forward.
01
Goal Setting & Prioritization
Getting clear on what you actually want to achieve — not just what's urgent — and building a prioritized roadmap to get there without burning out in the process.
02
Financial Clarity
Understanding your numbers — revenue, expenses, margins, cash flow — so you can make confident decisions rather than gut-feel guesses. Jon brings 30 years of financial analysis to this conversation.
03
Strategic Planning
Building a realistic one-page or full strategic plan that defines where your business is going, how it will get there, and what success looks like at each milestone.
04
Leadership Development
Growing your capacity as a leader — decision-making, delegation, communication, and building a team culture that supports your goals rather than creating more chaos.
05
Accountability & Follow-Through
Having someone in your corner who holds you accountable to the commitments you've made to yourself and your business. Most business owners don't have this — and it changes everything.
06
Navigating Growth & Change
Working through the specific challenges that come with growth — hiring, systems, structure, cash flow pressure, and the mental load of building something bigger than you started with.
07
Dream Planning
Pairing your passions with your skills and mapping a realistic path toward the business — and life — you actually want to build. Jon calls this "dream coaching," and it is often where the most meaningful work happens.
08
Problem-Solving & Sounding Board
Sometimes you just need a smart, experienced person to think through a problem with. Jon serves as a trusted thinking partner for decisions large and small — the kind of outside perspective most business owners don't have regular access to.
The Process
How a coaching
engagement works.
1
Free Discovery Call (30 min)
An honest conversation about where you are, where you want to go, and what's getting in the way. No pitch, no pressure. Jon listens first. This call is about figuring out if coaching is the right fit and what kind of engagement makes sense.
2
Intake & Current State Assessment
Before coaching begins in earnest, Jon gets a clear picture of your business — your financials, your operations, your team, your goals, and your biggest pain points. This isn't a formal audit, but it ensures the coaching is grounded in reality rather than abstractions.
3
Goal Setting & Planning Session
Together, you and Jon define what success looks like — in concrete, measurable terms. You build an initial roadmap: the key priorities, the milestones, and the actions that will move the needle. This becomes the north star for your coaching work.
4
Ongoing Coaching Sessions
Regular sessions (weekly, bi-weekly, or monthly depending on your needs) focused on progress, obstacles, and decisions. Sessions are structured but flexible — Jon follows your agenda while keeping you pointed toward the goals you've committed to.
5
Review & Evolve
At regular intervals, you and Jon step back to review progress, revisit goals, and update the plan. Businesses change. Good coaching changes with them.
Why Jon
Coaching backed by
real operational experience.
Most business coaches have never run a finance department, managed a supply chain, or led a team through a 25% growth year. Jon has done all of it.
Differentiator 01
He's been in the seat
Jon has held VP, Director, CFO, and Analyst-level roles across finance, operations, supply chain, and technology. When he helps you think through a problem, he's drawing on real experience — not a coaching certification curriculum.
Differentiator 02
Finance is always in the room
Most coaches stay at the strategy level. Jon brings 30 years of financial analysis to every conversation, so your goals and plans are always grounded in the numbers — not just vision and intention.
Differentiator 03
He can switch gears
If coaching reveals something that needs hands-on consulting — a process that needs to be built, a system that needs to be implemented — Jon can shift into execution mode. You don't need to hire someone else.
Common Questions
Business coaching
questions answered.
How is coaching different from consulting?
In coaching, Jon works alongside you — asking questions, helping you think through problems, and building your own capacity to solve them. In consulting, Jon does the work directly on your behalf. Both are valuable. Many clients blend the two: coaching for ongoing strategic clarity, consulting for specific execution tasks that need an expert's hands.
How often do coaching sessions happen?
It depends on the client. Some clients meet weekly for intensive periods of growth or change. Others prefer bi-weekly or monthly sessions for ongoing accountability and direction. Jon works with you to find the rhythm that keeps you moving without becoming another thing on your to-do list.
Is business coaching right for me if my business is struggling?
Yes — often that is exactly the right time. Coaching provides outside perspective and a structured process for working through challenges that can feel overwhelming when you're inside them. Jon has worked with businesses at many stages, including those going through genuine difficulty, and his finance background means he can help you get grounded in the real numbers quickly.
Do you offer coaching for wine industry businesses specifically?
Yes. Jon's 25+ years in the wine industry — spanning Kendall Jackson, Rack & Riddle Custom Wine Services, WX Brands, and J. Rickards Winery — give him deep credibility for wine business coaching. He understands the seasonal rhythms, the compliance complexity, the DTC dynamics, and the financial pressures specific to the wine industry in ways that a generalist coach simply cannot.
Where do coaching sessions take place?
Sessions can be in person for clients in Petaluma, Sonoma County, Marin County, and Napa County, or conducted remotely via video call. Many clients prefer a blend of both. Jon adapts to what works for you.