279: Ezra Firestone On Overcoming Adversity And How To Stay Sane Running Your Business

Podcast: Download (Duration: 55:30 — 63.8MB)

Building a brand around one person’s face creates a single point of failure that most founders never plan for. Ezra Firestone found out when Cindy Joseph, his business partner and the face of Boom on every product page and every email, died within seven days of learning her cancer had returned.

Ezra runs Boom by Cindy Joseph, a cosmetics brand for women over 50 doing around $20 million a year, the Shopify SaaS company Zipify, and the education company Smart Marketer.

This episode covers how Boom survived and grew afterward, the diversification that made it possible, his permaculture approach to business, and how he thinks about work-life boundaries.

Key takeaways

• Diversify who represents your brand before you have to. Boom had already started when Cindy first got sick.
• Reverse ageism exists. Women in their 60s do not want a woman in her 40s explaining aging to them.
• A price-raise sale made $500,000 in two days by announcing a 10% increase a week ahead.
• Split test front-end prices, not back-end. Back-end products absorbed a flat 10% raise untested.
• A two-week anticipation funnel doubled product launch effectiveness.
• Diversify ad objectives, not just creative. Facebook caps how many conversion ads one person sees.
• Content emails generate $40,000 a week without being sale emails.
• SaaS sells on a multiple of revenue, while ecommerce sells on a multiple of profit.

How Boom grew from $300,000 to $20 million

Ezra spent 2010 to 2014 attempting to launch Boom using content marketing, with 2014 being the first multiple six figure year.

2015 went from $300,000 to $3 million. 2016 went from $3 million to $17 million. The years since have held around $20 million.

His team went from 16 people to 103 across three companies over that period.

His own role changed from driver to navigator. His framing is that when you are on the road taking the turns, you cannot be above the road looking at the mountains ahead.

The place most do-it-yourself entrepreneurs get stuck is technology, bogged down in Facebook, Klaviyo, analytics, and Shopify themselves.

Why growth for its own sake is misguided

Ezra’s position is that the obsession with growth often leads to the demise of good companies.

Growth brings more inventory to fund, more overhead, and more stress and pressure on the person responsible for the whole operation.

His stated priorities run in order. First, enjoy his life and have fun, and have his team do the same.

Second, make genuinely good things that serve the world. Third, be profitable.

He does not care how big it gets or how profitable it is beyond that. Having a good time making good products that pay his team and his bills is winning.

The failure mode he describes is people getting large and shackled to operations that make them miserable.

My own experience matches it. Chasing aggressive growth targets with my wife produced repeated fights until we agreed to grow gradually, and the relationship improved immediately.

Why work-life boundaries require deliberate practice

Ezra calls the required skill eternal vigilance.

An internet business is available at all times, unlike a job you physically leave. The mental game of what could improve the business never closes.

Without explicit boundaries you show up to daily, the way you would a diet or a workout, the business becomes the backdrop of your entire life.

His own structure runs from waking to 10am for movement, meditation, and breakfast with family, work from 10am to 5pm, then social life and hobbies.

The exception he grants is launch mode, where you work intensively for weeks. The rule is that being unable to pick the business up and set it down deliberately becomes very hard over time.

Importantly, he considers this achievable as a solopreneur. He operated essentially alone from 2005 until hiring his first customer support person in 2009, and had one team member through 2012.

What happened when the face of the brand died

Cindy Joseph had one bout with cancer three years earlier, came very close to dying, then made a full recovery.

When it returned, she passed within seven days.

The personal side was severe. Cindy was a close friend who Ezra had lived with after moving to New York at 17, functioning as a bridge between his teenage and adult years and something of a second mother figure.

The operational side was chaos. Every email came from her, she did all the product demonstrations, and the front-end Facebook ads led with her story and her demos.

The 30-person Boom team was genuinely worried the company would fold or they would be fired.

They had to announce her death publicly and quickly, because she was a public figure and news outlets were beginning to pick it up, which created friction with her family.

Why partial diversification saved the brand

The decision that mattered was made years earlier, when Cindy first got sick.

They realized then that having the entire brand speak through one voice was a risk, and started making it about the experience of all women rather than one person.

She had not appeared in a video or audio for two years by the time she died.

The recovery work was still enormous: announcing the death to the community, rewriting every email sequence, modifying all front-end Facebook ads, and removing Cindy from the product pages.

Ezra’s own timeline was roughly six months of difficulty from July to January, three months of returning to normal, then three more months before he felt he had genuinely processed it.

Why the brand grew after losing its face

The diversification opened Boom to women who had not resonated with Cindy specifically.

They also discovered reverse ageism in the market. Women in their 60s do not want a woman in her 40s or 50s telling them about aging.

Being able to vary who presents on behalf of the company turned out to be an advantage rather than only a mitigation.

The other factor was a complete reassessment of every part of the business: product cost of goods, advertising, email strategy, and repeat purchase.

Why a failed sale process made the business better

After Cindy’s first illness, Ezra asked her directly whether she wanted to continue, given how close she had come to dying, or sell while the company was worth a great deal.

They agreed to sell and went all the way through due diligence with a buyer. She died before it closed, and the buyers withdrew.

He was not thinking about selling afterward, and the exercise itself proved valuable.

Going through diligence forces you to understand every factor affecting valuation and profitability, which he had not previously focused on. A year of operating with that knowledge is part of why the business grew.

What they changed to increase valuation

The factors that drive a valuation are repeat purchase rate, profitability, and diversification of both visibility and customer sources.

On margins, they renegotiated with every supplier, switched suppliers in some cases, and changed their packaging.

On price, they raised prices for the first time ever, since inventory and salary costs rise as a company grows.

How to run a price increase as a sale event

The tactic Ezra calls the best thing they have ever done made $500,000 in two days.

They told their community that prices were rising 10% in a week, and that buying now at current prices came with an additional 10% discount.

The framing is honest and specific. They had never raised prices, and growth had increased their costs.

How to test a price increase properly

Boom has only two front-end products people buy on first contact, both cosmetic sticks, because color cosmetics are far easier to sell to a new customer than skincare.

Everything else, fourteen skincare products, is back-end sold to people who already know the brand.

For the front-end products they split tested from a small increase up to a drastic one, against control.

A $10 increase produced the most profit and cut too heavily into new customers entering the funnel. They chose the medium increase, because audience size and revenue also affect valuation rather than profit alone.

The back-end products got a flat 10% raise with no testing at all, and it was fine. Those buyers already know and like the brand and are not price sensitive.

How to increase repeat purchases

Three changes drove it.

More sale events, now six a year.

More new products. Ezra’s view is that a key to scaling an established company is introducing three or four new products annually that you can cross-sell to existing customers and subscribers.

Then anticipation. They previously announced a new product on release day, and now spend two weeks building excitement through ads and emails about what is coming.

That single change doubled the effectiveness of their product launches.

Product launch advertising is roughly 95% people already on the email list or past customers, since lead generation to cold audiences does not convert well for launches. Cold traffic still leads with the flagship products.

How Boom does content marketing without SEO

Nothing is written with the goal of ranking. No keyword research happens before creating content.

They still add meta titles, meta descriptions, and an H1, and they do receive organic traffic.

The topics come from what their community is experiencing: skincare tips for aging skin, overcoming perfectionism, a battle with anorexia, hair graying, hormones changing through menopause, dating after divorce in your fifties.

The content pillars are tips, lifestyle, ambassador content, and sustainability, with a new ambassador program letting customers create videos about products and their own makeup routines.

They publish four posts a week with two writers on staff, investing roughly a million dollars a year in non-branded content marketing.

How content marketing actually monetizes

The content is amplified rather than left to sit. Facebook fans and subscribers see it, and it gets paid amplification on Google.

Three or four content emails a week generate around $40,000 a week in revenue, without being sale emails.

Every four to six weeks there is a product launch or a sale that monetizes the community more directly.

The compounding effect is what matters most. Sales convert better because the community is already engaged and seeing content in their feeds, so when they see a sale ad they respond.

They also track which articles and videos perform best on click-through, engagement, and purchase rate, then turn the winners into front-end pre-sell articles run to cold prospects, and add them to email automation sequences.

Ezra is candid that a lot of content simply gets buried on the blog and is never used again.

Why to diversify Facebook ad formats

Advertising costs have risen roughly 15% year over year for as long as Ezra has been online, and he does not expect that to change.

The cheap inventory right now is short form video under 15 seconds, on Instagram stories and Facebook mid-roll.

What most advertisers miss is mixing formats. Facebook will only show a given user the same video ad a few times.

Running images, GIF animations, and carousels alongside video means Facebook has more creative it is willing to show the same prospect, so you reach more of your audience.

Why to diversify ad objectives too

The same ceiling applies to objectives, and almost nobody accounts for it.

Most advertisers run only conversion-focused ads for add to cart, purchase, or email leads. Facebook shows only a certain volume of conversion ads to each prospect.

Putting even 10% of budget into brand awareness, dynamic product ads, catalog sales, or messenger objectives changes that.

Those objectives carry much lower CPMs, so a small share of budget reaches considerably more people than the same money spent on conversion ads.

How much creative you actually need

Ezra pushes back on the assumption that a large team is required.

Boom has been running roughly five videos for two years, edited and mixed in different ways.

One video editor or one graphic designer is genuinely enough, and both roles can be freelanced. Videos can be shot on an iPhone.

Refresh frequency scales with spend. Above a few hundred dollars a day you need to refresh often, and below that you do not. Zipify runs the same ads for months on roughly $50 a day.

Launching a new product needs three or four videos and a couple of images to test, and settles into one winner.

Ezra Firestone’s permaculture business model

Permaculture is a farming term meaning reuse every resource to its greatest benefit: capture rainwater for the garden, compost the food scraps.

His application is that people look outside for what they need without taking inventory of what is already around them.

The loop runs like this. He innovates in ecommerce with Boom, documents what works on the Smart Marketer blog, sells in-depth courses on it, and puts that money back into the ecommerce business.

Anything he builds for his own stores gets rolled into Zipify’s landing page builder or upsell builder, open-sourcing his own working solutions as products.

Why he moved from services to SaaS

Ezra ran an AdWords services agency from 2008 to 2012 and a development agency from 2011 to 2015, and describes services as possibly his worst business venture.

He sold three or four million dollars in services and made perhaps $30,000 in profit.

The cause was boundaries. He would sell a website, the client would ask for one more thing, he would agree, and there was never a container around the sale.

The WordPress plugin that changed his thinking cost about $30,000 to build and generated roughly $380,000 in revenue as a monthly subscription.

The lesson was that development works as a product on a subscription rather than as time sold. Nobody is buying Ezra, they are buying an application.

Why SaaS is harder than it looks

Zipify is by far the most difficult business he has been involved in, by a factor he estimates at fifteen.

The contrast with Boom is stark. Boom sells a tub with goo in it, and scaling means more tubs, more labels, and shipping them.

SaaS is a constantly changing code base requiring frontend engineers, backend engineers, QA, and project managers, with Shopify changing things underneath you.

Forty of his hundred-plus staff are Zipify developers, in his only physical office.

Why he built a SaaS company anyway

The strategic reason is asset creation rather than cash flow.

Smart Marketer is a cash flow business built around his persona, and could never be sold.

Zipify is an asset that could be sold one day, and SaaS businesses are generally valued at a multiple of revenue while ecommerce businesses are valued at a multiple of profit.

His framing of the larger game is resource generation. Cash flow businesses do not produce substantial wealth. Building or acquiring assets, growing them, liquidating them, and redeploying that capital does.

Even a small app needing a couple of developers and making $100,000 a year could be worth $500,000 to a million dollars liquid, which affords opportunities that cash flow alone does not.

How to run three companies at once

Each company has a project manager functioning as a COO responsible for ongoing operations, plus a president who moves across all three into key projects.

None are in the startup phase anymore, which is what makes it possible. Each has clear direction, consistent operations, and its own team.

Smart Marketer required the biggest change. Ezra was both lead educator and lead strategist, and as Boom and Zipify scaled he no longer had energy to keep courses current.

The solution was bringing in other educators, including Molly Pittman on paid advertising, with Ezra shifting to speaking and generating awareness while others handle the products.

Frequently asked questions

How do you build a brand not dependent on one person?

Diversify who represents it before you have to. Boom started featuring multiple women when Cindy Joseph first got sick, which is why the brand survived and grew after she died.

Should you raise prices on all products at once?

Split test front-end products where new customers enter, since raising too much reduces customer acquisition. Back-end products sold to people who already know you can typically absorb a flat 10% raise untested.

How do you announce a price increase?

As an event. Ezra Firestone told his community prices were rising 10% in a week and offered a 10% discount on current prices, which produced $500,000 in two days.

How do you make product launches convert better?

Build anticipation for two weeks before release through ads and emails describing what is coming. That change alone doubled the effectiveness of Boom’s launches.

Why diversify Facebook ad objectives?

Facebook limits how many conversion-focused ads any one prospect sees. Putting 10% of budget into brand awareness or messenger objectives reaches far more of your audience at much lower CPMs.

How much ad creative do you actually need?

Less than most people assume. Boom has run roughly five videos for two years, and one freelance designer or video editor is sufficient unless you are spending several hundred dollars a day.

Does content marketing need SEO to work?

Not necessarily. Boom writes entirely about their community’s lived experiences with no keyword research, amplifies it with paid ads and email, and generates around $40,000 a week from content emails.

Why is SaaS valued higher than ecommerce?

SaaS businesses are typically valued on a multiple of revenue while ecommerce businesses are valued on a multiple of profit, which produces a considerably higher number for the same business size.