Jonathon Blair

DTC Brand Fractional CFO | Follower of Jesus | Husband | Father of 3 | Fractional CFO | Leadership, Strategy & Productivity Nerd

www.FreeToGrowCFO.com

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🧔‍♂️ WHO IS FREE TO GROW CFO 
Outsourced CFO and Bookkeeping services for profit-focused DTC brands.   

Scaling a DTC brand is stressful. 

With messy books and no CFO on your team you run the risk of…  
-Hiring too quickly  
-Buying too much inventory 
-Scaling ad spend unprofitably 
-Running out of cash  

And that leads to stressful, sleepless nights. We don’t want that for you.  

Free to Grow CFO has given hundreds of DTC brands a plan for scaling alongside healthy profit and cash flow. Our plan will work for you too.

Fast, Insightful Reporting.  Proactive Strategic Advice.  From DTC Finance Experts.  
-M&A -Debt & Equity Funding 
-Accurate Financials by the 15th 
-Planning, Forecasting, Budgeting 
-Financial Dashboards and KPI Tracking   

All delivered through our proven, ready-to-implement “Free to Grow CFO Process”.

📈 WANT TO INCREASE PROFIT AND CASH FLOW AS YOU SCALE?
Book a Call Now → https://freetogrowcfo.com/book-a-call

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Founder | Fractional CFO

www.freetogrowcfo.com

Fractional CFOs for High Growth Direct-to-Consumer Brands

Outsourced, part-time CFO services for high growth D2C brands, designed to help you scale your business with confidence.

You don't have to suffer through another sleepless night worrying about making difficult business decisions alone.  Hire a Free to Grow CFO and get the financial insights you need to make fast, effective business decisions with confidence.

Get access to the CFO you need to scale your business without the full-time salary:
-Strategic Planning
-Forecasting & Projections
-Cash Strategy & Fundraising
-Financial Statement Analysis

Jon Blair

I'm hearing lots of people say that DTC brands "must go omni-channel." I gotta be honest, I think this is BS and I don't agree.

Now to be clear, if you have goals to get to $50m+ in annual sales, then yes you probably need to go omni-channel because physical retail will be required to hit those numbers.

But there are plenty of 8-figure <$50m niche DTC brands that crush it.

And there's nothing wrong with staying DTC-only and limiting your TAM.

You can still build a great business that way.

But just be honest with yourself about the fact that if you want to grow to $50m+ you're likely going to need additional channels beyond DTC.

Most Fractional CFOs say a DTC brand should have a 13-week cash forecast. I think this is BS, here's why...

Ok - so every time I post about this, people freak out and don't hear the point I'm making.

So please read carefully.

Do some brands need a 13-week cash forecast?

Sure.

Does every brand need a 13-week cash forecast? 

Not at all. 

Start by asking two key questions:

1️⃣ Do I actually need weekly visibility into cash flows, or is monthly enough?

You'd be surprised how often monthly visibility is enough for the decisions you currently need to make.

2️⃣ What time horizon is appropriate for the decisions at hand?

If your business decisions don’t require weekly insights over a 13-week period, building that kind of forecast is just a waste of time. 

For example - if you just need the weekly visibility to approved weekly AP payments, I often find that 2-6 weeks of visibility is plenty.

What's the point I'm making with all this?

𝗕𝘂𝗶𝗹𝗱 𝗳𝗼𝗿𝗲𝗰𝗮𝘀𝘁𝘀 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰𝗮𝗹𝗹𝘆 𝘁𝗼 𝘀𝘂𝗽𝗽𝗼𝗿𝘁 𝗺𝗮𝗸𝗶𝗻𝗴 𝘁𝗵𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀 𝗮𝘁 𝗵𝗮𝗻𝗱 - 𝗻𝗼 𝗺𝗼𝗿𝗲, 𝗻𝗼 𝗹𝗲𝘀𝘀.

𝗔𝗻𝘆𝘁𝗵𝗶𝗻𝗴 𝗺𝗼𝗿𝗲 𝗶𝘀 𝘄𝗮𝘀𝘁𝗲𝗱 𝘁𝗶𝗺𝗲.

And let's be real - time is not something you can afford to waste right now.

--

Hi, I'm Jon Blair founder of the DTC Finance and Accounting firm Free to Grow CFO.

Want more tips on growing a profit-focused DTC brand? 

Give me a follow.

Want to learn more about how Free to Grow's Accountants and CFO's can help you increase profit and cash flow as you scale?

Shoot me a DM.

Until next time, scale on!

In the past year I've audited 100+ DTC brands' financials and Shopify data and I'm shocked by my findings...

Brand founders by and large don't understand that there is much more to ad spend profitability than simply tracking the impact on company-level contribution margin.

What are they missing?

You MUST bifurcate contribution margin into new customer and returning customer segments.

Why?

To understand how profitable your new customer orders need to be.

Why does this matter?

Because the answer to - "what CAC can I afford?" is determined by answering "how high does my first-order profitability need to be?"

And this can only be answered by understanding whether or not returning customers drive enough margin dollars to SUBSIDIZE a lower first-order profit.

Without this "returning customer subsidy," you must rely solely on first-order profitability as the driver of company-level profit.

Do you wish you had a better understanding of these dynamics for your brand?

Consider hiring an expert DTC Fractional CFO to help.

--

Hi, I'm Jon Blair founder of the DTC Finance and Accounting firm Free to Grow CFO .

Want more tips on scaling a profit-focused DTC brand? 

Give me a follow.

Want to learn more about how Free to Grow's Accountants and CFO's can help you increase profit and cash flow as you scale?

Shoot me a DM.

Until next time, scale on!

If your DTC brand doesn’t have meaningful 3–6 month LTV (in 𝘮𝘢𝘳𝘨𝘪𝘯 𝘥𝘰𝘭𝘭𝘢𝘳𝘴) you need to be first-order profitable.  Guaranteed.

Losing money on acquiring a new customer basically means you’re “loaning” your business cash—hoping to get it back through repeat purchases (ie, LTV).

But there are financial dangers you need to watch out for if your CAC payback is too slow:

• If customers don’t buy again fast enough, you run out of money before the payback ever happens.
• The slower the payback, the slower you can reinvest into new customer acquisition.
• Scale stalls because you can’t afford to keep spending on ads.

Think of it like this: 

You can loan a friend $100 for 2–3 years.

But if you’re also loaning $100 to more friends every week, you’ll eventually run out of cash because you are loaning out money faster than you are collecting it back.

Now flip this: 

If your friends pays you back in 7 days, you can immediately redeploy that same $100 into the next week's loan. 

Cash keeps circulating—and if your are charging interest, growth can compound.

Ad spend works the same way. 

If your payback cycle is slower than your rate of new customer acquisition, you become unprofitable and cash runs out. 

If it’s faster, you can reinvest and scale with positive profits and cash flow.

The morale of the story?

The faster your repeat purchase pays back new customer losses, the faster you can grow. 

If that payback isn’t happening in 3–6 months, first-order profitability isn’t optional—it's required.

The fastest way to manage CAC payback cycles is by working with an expert DTC CFO who speaks ad spend. 

That’s exactly what we do at Free to Grow CFO 

In DTC, growth lives and dies by paid media. 

That’s why our CFOs are experts in ad spend profitability—channel by channel, cohort by cohort. 

We go beyond surface metrics to help you scale what works, cut what doesn’t, and hold your agency accountable. 

Got anything to add?

Jacob P. Liam Veregin Bernardo Caixeta Dylan Byers Thomas Gleeson 🦸 Karl O'Brien 🦸 Jeff Lowenstein

"Real estate isn’t dead. You’re just underwriting it wrong."

That’s one of the biggest takeaways from my upcoming Free to Grow CFO Podcast episode.
 
I sat down with Ryan Kelly  — investor, broker, and mortgage lender — to talk about what’s actually happening in today’s market and how brand founders should be thinking about deploying profits outside their business.
 
We get into the operator mechanics of real estate investing:
 
• Why “nothing pencils” usually means you’re looking in the wrong market  
• The underwriting mistakes new investors make  
• Why you need an investor-focused agent, not your personal home agent  
• How to structure deals so they work on today’s numbers, not future hope  
• The difference between active income strategies and true passive plays
 
Scaling your brand is step one.
 
Turning profit into distributable cash is step two.
 
Deploying that cash into appreciating assets is step three.
 
If you’re a founder generating real cash flow and wondering how to turn it into long-term wealth, this episode will give you a clear starting point.
 
🎙 Drops next week.  

🔔 Like and subscribe to the Free to Grow CFO Podcast to be the first to know when the episode drops: 
📺 YouTube: https://lnkd.in/eFz-S425 
🎙️ Apple Podcasts: https://lnkd.in/eKsJzCfK 
🎙️ Spotify: https://lnkd.in/e85eV5p3

Debt capital has never been more accessible to DTC brands.
 
In today’s ecom world, it’s everywhere.
 
Shopify Capital.  
Revenue-based financing.  
Credit cards with big limits.
 
It takes minutes to apply.  

The cash hits fast.
 
It’s at your fingertips.  

It’s alluring.
 
But here’s the uncomfortable truth:
 
Just because you can use debt doesn’t mean you should.
 
Not all growth should be financed.  

Not all risk should be levered.
 
Access to someone else’s cash changes how you think.
 
It subtly nudges you to go bigger.
 
“Let’s push spend harder.”  
“Let’s double the PO.”  
“Let’s hire ahead of revenue.”
 
Not because the data supports it.
 
But because the money is there.
 
Here’s a simple discipline I recommend to founders:
 
1️⃣ Remove debt from the equation entirely.  
2️⃣ Ask: What decision would I make based only on the data and my real risk tolerance?  
3️⃣ Then bring debt back in and ask: Do I want leverage to support that same decision?
 
Where brands get into trouble isn’t just using debt.
 
It’s using debt to justify a decision they wouldn’t have made without it.
 
Debt is an amplifier.
 
If your unit economics are strong and your cash flow is disciplined, it can accelerate growth.
 
If your economics are fragile or emotional, it will expose that fast.
 
Leverage doesn’t fix business models.
 
It magnifies them.

🎙️ We dive into this topic and more on the latest episode of The Ecom Scaling Show.

Give it a listen if you’re considering taking on debt this year ---> https://lnkd.in/dRFTShjs

Most DTC brands don’t run into trouble because their forecast was “too aggressive.”

They run into trouble because they built their entire business around the assumption that the forecast had to come true.

Here’s what that usually looks like:
→ You predict $10M in Q4
 → You place POs to support it
 → You take on debt to finance it
 → You hire to operate at that scale

Now you’re boxed into one outcome.

Hit the number? You are a success. 

Miss it? You’re managing a cash crisis.

That’s not strategy. That’s a binary bet.

Smart operators don’t plan around prediction.

They plan around cause and effect.

They ask:
-If CAC rises 20%, what happens to cash?
-If revenue lands 30% below forecast, are we still solvent?
-What revenue actually supports this inventory decision?

That shift changes everything.

In my latest newsletter article, I break down why scenario-based planning is the difference between scaling profitably and getting crushed by growth — and how to build financial optionality instead of financial fragility.

If you’re heading into your next growth stage, this is worth the read.

👇 Full article below.

View newsletter: The Free to Grow Newsletter

The biggest failure I see in DTC business planning isn’t a lack of ambition. It’s the assumption that your plan will go exactly as expected. In realit

Open article: Stop Treating Your Plan Like a Prediction  by Jon Blair • 4 min read

Stop Treating Your Plan Like a Prediction

Profit from your brand doesn’t make you wealthy. What you invest it into does.
 
That’s a core theme from the latest Free to Grow CFO Podcast episode.
 
I sat down with real estate investor and broker Ryan Kelly to talk about how founders should think about deploying the cash flow their brand generates.
 
Not from a hype perspective.
 
From an operator perspective.
 
We get into:
 
• Why running a rental property is a business  
• The biggest traps new real estate investors fall into  
• Why deals need to work on today’s numbers  
• Why the agent you work with matters more than most investors realize
 
If you’re building a profitable brand, the question eventually becomes:
 
What are you doing with the cash your brand produces?

If you're a founder thinking about getting into real estate investing, this episode is a great starting point.
 
🎧 Episode is live.  

Listen here → https://lnkd.in/eNKf_EvR

Centric Software

Senior AI/ML Engineer

Global Max Labs

Nike

Senior Innovation Engineer

AWM Smart Shelf

Full Stack Software Engineer

Danson Development

BuildFire

Business Development Manager

Coastline Real Estate

Realtor

Morgan Skenderian

As an associate at Morgan Skenderian, I specialize in selling apartment buildings as investments. I compile highly detailed proposals for dispositions, including financial models for rent roll, income and expenses, ROI matrix analysis based on multiple options for sales price, 1031 exchange benefit comparisons, and return on equity models. 

In order to better serve sellers, I consistently assemble Comparative Market Analysis reports for apartment buildings, which includes working regularly with CoStar, Loopnet, and MLS—always verifying accuracy on the provided comps. I am consistently in connection with local apartment owners and property managers conducting rental Market Surveys; this information allows me to better advise clients.

Each week, I consult face-to-face with 2 to 5 new property owners on creative ways they can increase their NOI. I also regularly assist buyers with their due diligence on new acquisitions. I work hard to identify key investments – both on and off market – tailored to my buyer’s specific goals. 

At Morgan Skenderian, I created opportunities for technology advances company-wide. I also invented and established a unique system to double my productivity for database compilation using outsourcing and automation software.

Associate

Fitzpatrick + Prince

As a Realtor at Fitzpatrick + Prince, I earned success in residential single family sales, short sales, and luxury deals in over 5 counties up and down California’s coast, frequently managing up to 40 listings at one time. In 2012 alone, I successfully closed 30 deals. To add value to the properties, I coordinated professional photography, HD video tours, property websites, and property brochures. 

To add value to the brokerage as a whole, I strategically created $10M in additional deal flow by focusing on commercial and income property analysis.  During my time at Fitzpatrick + Prince, I gained a meticulous knowledge of real estate contracts and real estate law and was able to efficiently coordinate closings on my own transactions.

As a Resident Relations Specialist, I supported the company’s marketing by posting ads, touring prospects, and answering inquiries over the phone. I approved prospects, prepared leases, and managed all administration. I actively followed up with all resident and prospective resident inquiries in an apartment community of 264 apartments and over 500 residents. I ensured resident satisfaction by promptly addressing resident complaints, preparing service requests, and coordinating with the maintenance team to confirm that maintenance issues were handled professionally. In my time there, I also successfully completed two five-star customer service training courses which furthered my expertise in the field. 

Not only was I able to serve residents well at UDR, but I also played an integral part of increasing the company’s revenue. I regularly conducted market research to make sure we had the most competitive pricing, while still ensuring the largest profit.  I also increased revenue by over $30K a year by suggesting we stop waiving fees for applications and begin charging pet rent. I continually negotiated renewals over market value, while still leaving residents satisfied with their renewal rate, increasing revenue by over $40K a year.

Resident Relations Specialist

As a Senior Innovation Engineer at Nike, I spent years refining my skills in the full innovation process, from ideation all the way to large scale production, with a particular focus on AI and machine learning.

I have worked on and lead projects across several domains including Computer Vision, Natural Language Processing (NLP), Machine Learning for Audio Processing, and Time Series predictions. I'm also well versed in both supervised and unsupervised learning pipelines, real-time inference apis, and have worked with GAN models for audio, images, and text. 

An important part of my approach to these technologies is to not just stay at a high level but to go into the low-level details to understand how things work from first principals. Diving into things like model architectures, the underlying math, and optimization techniques which I find both fascinating and intuition building. This helps build a clearer understanding of what these models can be capable of, and what is needed to create valuable outcomes.

There are a number of projects that I've worked on that are confidential due to NDAs. However, some of the work I can discuss includes a computer vision IoT-based proof of concept that I co-developed with a fellow engineer and was featured on Fox News during the NRF conference. I've also deployed machine learning at scale for training pipelines and real-time inference on Nike App's Visual Search. In addition, I developed a novel way for live stream hosts to interact with their audience, irrespective of the size of the audience. For this, I architected, developed, and deployed a scalable NLP real-time semantic search capable of handling live feedback from 100,000 concurrent viewers on SNKRS Live. Lastly, my team and I built a solution for an ongoing time series data pipeline for machine learning predictions at massive global scale, resulting in significant financial & time savings in operations.

I’m a big proponent of Outcome Driven Innovation, and I’ve started to partner with companies with $1M+ in gross revenue a year. So if your company is looking to leverage AI to create valuable outcomes for your existing customers, send me a message and let’s connect!

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