Oct 4, 2020 · 27m · top-founders
SandHill Dev Sells $55k/mo Side Project for $1m+, Now Building 4 Other Products $3.6m Run Rate
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, Sandhills Development founder Pippin Williamson discusses managing a $3.6 million ARR bootstrapped software portfolio with Nathan Latka. Williamson breaks down the strategic sale of Restrict Content Pro to iThemes, the unit economics of core products like AffiliateWP, and his philosophy on sustainable remote operations.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 33.6% of the talking time here. How this is scored →
Nathan as informed peer 4.8 Guest teaching 2.6 Guest disagreement 0.3 Nathan pushing back 1.6
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:25 Resisting quick sale pressure
Pippin politely rejects the premise that he should flip his flagship product AffiliateWP just because someone might pay a 3x multiple.
Hardest push from Nathan ▶ 8:09 Challenging guest on potential sale of flagship productNathan directly presses whether Pippin would take an immediate 3x multiple offer on his $1.5M ARR product after selling his side tool.
Biggest teaching moment ▶ 15:14 Correcting monthly billing assumptionPippin informs Nathan that the company uses exclusively annual billing with grandfathered discount tiers rather than standard SaaS monthly subscriptions.
Nathan holds their own ▶ 12:48 Dissecting net revenue from gross payment volumeNathan instantly breaks down the distinction between $78k in gross processing volume and the actual $2,300 net revenue derived from their 3% take rate.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Podcast Promotion and Latka Membership Overview | 1 | 0 | 0 | 0 | Introductory promo and host background framing with minimal substantial interaction prior to kicking off the interview. | |
| The Strategic Divestment of Restrict Content Pro | 5 | 3 | 1 | 2 | Nathan digs into the divestment multiple and valuation philosophy, while Pippin transparently breaks down why 2-3x annual revenue made strategic sense for both buyer and seller. | |
| Sandhills Revenue Composition and Flagship Product AffiliateWP | 5 | 2 | 1 | 2 | Nathan tests whether Pippin would also sell his flagship product AffiliateWP, but Pippin politely reaffirms his commitment to building long-term. | |
| Bootstrapping Philosophy, Cash Reserves, and Profit Margins | 4 | 3 | 0 | 1 | Pippin explains the discipline of bootstrapped profit margins and capital reallocation after divesting a core product line. | |
| Product Portfolio Deep-Dive: EDD, WP Simple Pay, and Payouts Service | 6 | 4 | 0 | 3 | Nathan clarifies gross processing volume versus net revenue on the payouts tool, catching that 78k was volume and calculating actual gross revenue at 3%. | |
| AffiliateWP Customer Metrics and Annual Pricing Architecture | 6 | 5 | 1 | 3 | Pippin explains that pricing is purely annual rather than monthly, correcting Nathan's initial per-month customer value assumptions and breaking down grandfathered discounts. | |
| Acquisition and Equity Structuring of WP Simple Pay | 5 | 2 | 0 | 1 | Nathan and Pippin explore the mechanics of acquiring WP Simple Pay via upfront equity with waived vesting based on historical sweat equity. | |
| Remote Organizational Architecture and Global Engineering Team | 5 | 3 | 0 | 2 | Nathan annualizes monthly churn numbers, while Pippin details cross-selling pathways across complementary products in the portfolio. | |
| Go-To-Market Channels and Affiliate Program Economics | 6 | 2 | 0 | 2 | Nathan rapidly does the back-of-the-envelope math on affiliate payout economics to deduce top-affiliate generated revenue. | |
| Famous Five: Leadership Insights and Work-Life Balance | 5 | 2 | 0 | 0 | Pippin shares reflections on avoiding burnout and working reasonable hours, followed by Nathan's comprehensive outro summary. |
Statements from this episode (24)
Restrict Content Pro generated $50k-$55k monthly revenue before its sale
“For last month, zero because the sale actually went through before last month, but at the time that we sold it was doing about 50 to 55,000 a month.”
Sandhills Development retained its entire team after selling Restrict Content Pro
“So we didn't transfer any of our team members with the product only the product. So we effectively were able to hire three new people without actually hiring anybody. Cause we took the people that were working on the product and have put them onto some of our …”
Sandhills Development sold Restrict Content Pro for 2x to 3x annual revenue
“We did. I can't say exactly where we got due to our contract. But it was definitely in the range of what we wanted.”
Liquid Web subsidiary iThemes acquired Restrict Content Pro in September 2020
“It is public. It all went live on September first. And so if anybody wants to check it out, you can go to sandhillsdev.com. We wrote a blog post there. And the buyer was iThemes, iThemes.com, which is a, one of the brands under the liquid web family.”
Sandhills Development generates $311,000 monthly across its four software product brands
“So we run, we still run four separate product brands. And so that 311 is a combination of all four of those. With the largest being about a 130 to a 150,000 and the smallest being one to 2000 a month.”
Sandhills Development has no plans to sell its top earner, AffiliateWP
“At this point we have no plans to sell it. It is something that we're having a lot of fun with and it is our biggest moneymaker for sure.”
Sandhills Development is fully bootstrapped and privately owned with zero outside capital
“We are a hundred percent bootstrapped, self-funded business. We have no outside investment and we're all privately owned.”
Selling Restrict Content Pro eliminated the majority of Sandhills Development's profit margin
“And when we sold off restricted content pro, That was basically the loss of that revenue was majority of our profit margin.”
Sandhills Development projects a 10% to 20% profit margin by year-end 2020
“I think we'll see 10 to 20% profit margin by the end of the year.”
Easy Digital Downloads generates approximately $70,000 in monthly recurring revenue
“Easy digital downloads, which is a e-commerce platform for selling digital products. And it does about 70,000.”
WP Simple Pay generates $40,000 to $45,000 in monthly recurring revenue
“WP simple pay, which is a simple e-commerce tool, basically allow simple payments through stripe.com for website or business owners. And it does about 40 to 45,000.”
Sandhills' Payouts Service processed $78,000 at a 3% net cut last month
“78,000 was the amount that we processed for other businesses, and we take a three percent cut. At three percent after all fees.”
AffiliateWP serves approximately 10,000 to 15,000 active customers
“Affiliate WP is around the I think. 10 to 15,000 active customers at this point.”
Sandhills Development bills exclusively annually for AffiliateWP, offering no monthly plans
“Yeah, so everything, we don't do any monthly values. We do everything in annual.”
Easy Digital Downloads is actively installed on 50,000 to 75,000 websites
“To date affiliate sorry, easy digital downloads is installed on somewhere between 50 and 75,000 websites.”
WP Simple Pay currently maintains 4,300 active paying customers
“It currently has 4300 active customers.”
Sandhills Development acquired WP Simple Pay through an equity swap
“We basically came to an agreement where he bought into the company and his, basically his selling the price for WP Simple Pay was equity. So we gave him equity in the company and he gave us WP Simple Pay.”
WP Simple Pay generated $22,000 to $24,000 monthly revenue at acquisition
“It was doing about 22 to 24,000.”
Sandhills granted WP Simple Pay's founder fully vested equity upfront upon acquisition
“At four sandals development, we do have a vesting period for all owners. There are, there's five of us partners. But with his, we actually considered his fully vested because basically his value was the five to eight years of WP simple pay that he had run befo…”
Sandhills Development averages 4% to 5% monthly churn across its core products
“So I roughly average these before we hopped on and we do about four to five percent.”
Sandhills upselled customers across its portfolio into AffiliateWP and its payout service
“If we're going from any of our products besides the affiliate program, we'll upsell to affiliate WP. If they are an affiliate WP customer, then we upsell them to the payout service.”
AffiliateWP sees 15 to 20 commission-earning affiliates in a given month
“So our, we don't, so our affiliate program, I'll be honest, is a little bit small, but basically I would say we have on any given month, 15 to 20 people that earn at least a dollar. But then we'll have about three to four that are doing the somewhere between 5…”