The succession market was the bet

We started as a marketplace for small businesses in the United States. The SBA counts millions of small employers nationwide; a large share of baby-boomer owners are approaching retirement without a family successor lined up. Profitable companies are coming to market. Buyers were already looking. The gap was discovery, diligence, and a path from first glance to close.

Entrepreneurship through acquisition was having a moment for good reason: operators with capital and skill want cash flow now, not a five-year bet on product-market fit from zero. We built recommendation algorithms to surface the freshest listings that matched each buyer's investment criteria, not just industry and price. Analytics on every listing and a seller workflow helped owners standardize financials early, with permission, so buyers could judge fit before the formal diligence packet.

Canada followed the same product story. We built trust and liquidity through listings and matching first, then layered payments and escrow.

Brand, transparency, and owner data

We started with a simple brand and structured financials on every listing. The logo had to read trustworthy on a listing card and in a diligence room. Transparency was the product philosophy: put the data up front so people could make informed calls from the listing itself.

That meant working closely with owners to collect accurate numbers, with their permission, and keep them current as the business changed. We continued to refine that with the Openfair service team so buyers had better context and sellers could share what actually helps someone decide.

With my co-founder and the team, we mapped buyer and seller journeys to find where deals stall: search, outreach, NDA binders, sloppy teasers. That exercise shaped search and discovery, and how we talked to owners about listing. Some did not see themselves as advertisers even when they needed to sell. We made onboarding straightforward with AI-assisted listing flows to help them move their story into a publishable asset. Others already ran on their own systems, so we built integrations instead of asking them to rip and replace.

Brand in product

Buyers see the same restrained wordmark on listing cards as in diligence. Trust started on screen one, before anyone opened a data room.

• Openfair wordmark lockup on white field: Wordmark
• Openfair search home with map and listing cards on desktop: Search and discovery

Matching buyers to the right listing

Search, filters, and listing cards with revenue, profit, and asking price before the click. Detail pages carried documents, seller context, and the marketing assets owners chose to attach.

The core experiment was recommendation: ranking listings so each buyer saw likely fits first, weighted by freshness, financial profile, and the softer signals that matter in small-business sales. Industry and budget were table stakes. We iterated on what predicted a saved deal versus a dead click.

Each release had to move a buyer closer to a saved opportunity or a seller closer to a published listing. Work that did not connect to one of those loops waited.

Scale what worked

We reached $1M+ ARR in twelve months. I hired and structured the first teams around search and listings, matching and notifications, and seller onboarding.

What I would repeat: revenue, profit, and asking price on every listing card before polish elsewhere. Track activation on saved and matched deals, not raw sign-ups. Keep brand and listing cards on the same restrained tone so trust started on screen one.

What I would sequence differently: ship seller publish flows in the same cadence as buyer search. Liquidity needs both sides from week one, even when sellers stay invite-only at launch.