Business Coaching

The business skills
nobody teaches you.

Every month, Startup Sherpa clients join a live coaching session built around one question: what do you actually need to know to run a successful business — and how do you apply it right now?

The program

Structured learning that compounds.

Most business owners learn by trial and error — making expensive mistakes that a little knowledge would have prevented. The Startup Sherpa coaching program is designed to systematically close the gaps that cause businesses to struggle and fail.

Every month covers a different topic directly relevant to running and growing a business. New sessions are added regularly as the business landscape changes and as our clients grow — so whether you're in your first year or your fifth, there's always something relevant to where you are right now.

  • 60 minutes live on Zoom — every month
  • 30 minutes structured presentation on the month's topic
  • 30 minutes open Q&A — bring your specific questions
  • Recorded — available within 24 hours if you miss it
  • One guest referral pass per session — bring a fellow business owner
  • Included in every package — Basecamp, Ascent, and Summit

Craig on the coaching program — what it is, why it's built this way, and what it does for your business over time

Sample topics

A taste of what we cover

Topics are added and refreshed regularly. Here's a sample from the current program — practical, specific, and directly relevant to the challenges growing businesses face.

Session 01
The Five Numbers That Drive Every Business

Most business owners focus on revenue. The ones who grow fast focus on five specific levers — leads, conversion rate, transaction frequency, average sale value, and margins. Improve each by just 10% and your profit doesn't go up 10%. It compounds. This session shows you what those levers are and how to start pulling them.

Session 02
Business Buckets — Never Get Caught Short Again

Cashflow problems don't usually come from a bad business. They come from money sitting in one account with no plan for where it goes. This session introduces a simple allocation system — separate buckets for tax, operating costs, owner's pay, and profit — so you always know exactly where you stand and nothing catches you off guard.

Session 03
Pricing for Profit

Most business owners price by gut feel or by copying competitors. Neither works. This session covers how to price your products and services so the business actually makes money — not just revenue — and why the fear of charging what you're worth is costing you more than you think.

Session 04
Understanding Your P&L and Balance Sheet

Your accountant can read your financials. Can you? This session demystifies the numbers — what your P&L is actually telling you, what the balance sheet means, and how to use both to make better decisions before problems show up in your bank account.

Session 05
Stop Being the Bottleneck

If your team can't make a decision without you, you don't have a business — you have a job with staff. This session covers how to build decision-making frameworks your team can follow, how to train people to solve problems without interrupting you, and how to protect your time for the work only you can do.

Session 06
Build a Tech Stack That Works While You Sleep

The right combination of tools, automations, and AI can make a team of two do the work of ten. This session covers how to audit what you're currently using, identify the gaps, and build a lean, leveraged tech setup that buys back your time without blowing your budget.

Topics rotate and evolve — new sessions are added regularly to reflect current business conditions, tax changes, and what our clients are working through.

Let's be straight

This is group coaching, not 1-on-1.

You won't have Craig on speed dial. There are no emergency calls, no personal sessions on demand, and no unlimited access to Craig outside the monthly session.

What you will have is a structured monthly session with a room full of business owners working through the same challenges you are — and someone at the front who has actually built and sold businesses, not just studied them.

The group format is a feature, not a limitation. The questions other business owners ask are often the exact questions you didn't know to ask. You'll learn from the room as much as from the presenter.

✓   What it is
  • Monthly live group session on Zoom
  • 30 min structured topic + 30 min open Q&A
  • Recorded — available if you miss it
  • Evolving library of practical business topics
  • Included in every package
  • One guest pass per session
✗   What it isn't
  • 1-on-1 coaching on demand
  • Unlimited access to Craig
  • A replacement for professional advice
  • Generic business theory
  • A separate paid add-on
  • Closed to your network
The Summit difference

On the Summit plan, it feels different.

Summit clients receive everything above — plus a monthly one-on-one CFO meeting with Craig. That's a private session focused entirely on your business: your numbers, your strategy, and your specific challenges and opportunities for the month ahead.

It's not group coaching. It's as close to having a personal CFO and business advisor as most growing businesses will ever experience.

If your business is turning over $1M or more and you want that level of support, Summit is built for you.

Summit plan

Full CFO partnership

$2,350/month
For businesses $1M–$5M in annual turnover
  • Monthly live group coaching webinar
  • Monthly 1-on-1 CFO meeting with Craig
  • Monthly bookkeeping and management reports
  • Cashflow forecasting and KPI dashboard
  • Structure and strategy advice
  • Unlimited support calls
  • Full video course included
Book a discovery call →
Why it's in every package

This isn't a bolt-on. It's a foundation.

We include the coaching in every package because accounting without business education is only half the job. We can keep your books clean, lodge your BAS, and minimise your tax — but if you don't understand how to grow your business, those numbers will stay small.

The accounting keeps you compliant. The coaching gets you to your first million.

Our goal for every Startup Sherpa client is the same — your first $1,000,000 in annual revenue. That's not a ceiling. It's a starting point.
5
businesses started by our founder personally
2
businesses sold — real exit experience
10+
years coaching founders across every industry
$1M
the revenue goal we set for every single client

Coaching is included in every package

Choose the level that matches where your business is today. All three include monthly live coaching — Summit adds a personal monthly CFO meeting.

Basecamp
Under $250,000 annual turnover
$395/month
Monthly group coaching webinar included

Foundation compliance, BAS, tax returns, and monthly coaching to build your business knowledge as you grow.

Ascent
$250,000 – $1,000,000 annual turnover
$1,395/month
Monthly group coaching webinar included

Everything in Basecamp plus monthly bookkeeping, management reports, quarterly CFO meetings, and annual tax planning.

Summit
$1,000,000 – $5,000,000 annual turnover
$2,350/month
Group coaching + monthly 1-on-1 CFO meeting

Everything in Ascent plus monthly CFO meetings with Craig, cashflow forecasting, KPI dashboard, and strategic advice.

Ready to start building the skills that compound?

Every Startup Sherpa package includes monthly live coaching. Choose your level and get started today.

View all packages → Take the quiz first