0 to $9.5M Series A: Inside Guidesly’s Journey with David Lord

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

Crazy idea…

I’m pouring more time into The LA Grind and weighing the best future for the Just Go Grind Newsletter and Podcast. I might keep building it myself, bring in a partner, or even sell it to a new owner.

Before I decide, I’d like to gauge real interest from this community. Please pick the option that fits you in the poll below.

I’m excited to bring you the latest Just Go Grind Podcast interview with David Lord, a serial entrepreneur and the Founder & CEO of Guidesly, a platform where you can book the world’s best outdoor trips & activities.

David Lord grew up chasing trout and tarpon, spotting the pain points of working guides long before most tech founders ever booked a charter.

Today he runs Guidesly, a vertical-SaaS marketplace that helps guides own their customer relationships, fill calendars, and automate marketing with JackAI.

In my conversation with David, you’ll hear how a stubborn “no-asshole” rule shapes every hire and investor decision, why David waited until after a $9.5 million Series A to spend a dollar on brand, and what it takes to cut churn to almost nothing when your customers live on the water.

If you are building a marketplace, wrestling with SaaS retention, or looking for a durable moat, this episode is for you.

And, if you’re interested in going through the same accelerator, 43North, that David went through with Guidesly, getting a $1M investment in the process, apply today, applications close July 9th!

Thank you to today’s sponsor, MACROFIT, for supporting the show!

Listen to David’s interview on YouTube, Spotify, or Apple Podcasts.

Let’s dive in.

MACROFIT Is Building the Future of Fitness Hardware + Subscriptions

I use the MACROFIT Home Gym every day and it’s one of the best products out there for bodyweight and calisthenics training.

The team is now raising to turn MACROFIT into a holdco of premium fitness tech products with strong recurring revenue. They just acquired Flexia Pilates, a connected pilates platform tapping into one of the fastest-growing categories in wellness.

Next up: the launch of Newton, their smart strength trainer — think Tonal, but way better.

More on the acquisition here: LinkedIn Post

Check out MACROFIT: www.joinfitapp.com

Founder: Mike DeVerna (Former COO of Wag!, $400M+ raised)

• Adopt a strict “no-asshole” policy. Vet every investor and hire by calling past partners; if the references say they’re difficult, walk away.

• Solve a problem you know cold. David built in fly-fishing because decades on the water let him spot pain points outsiders miss.

• Ride enabling tech waves. Vertical-SaaS toolkits, Stripe marketplaces and React Native made a once-impossible platform feasible. Watch for similar unlocks in your niche.

• Time fundraising to claim the market. He raced to raise once a federal report showed guiding was a $50 billion U.S. market, knowing fast capital would pre-empt copycats.

• Curate a value-add cap table. Hand-pick angels and funds that bring sector knowledge, AI talent or distribution, not just money.

• Filter hires for genuine passion. Require candidates to love the craft your customers live for; it keeps culture tight and service authentic.

• Leverage accelerators strategically. 43North gave capital, a supportive Buffalo network and early enterprise customers. Pick programs that fill your biggest gaps and lean in.

• Delay brand spend until Series A. Before product-market fit, every marketing dollar can be wasted; he waited, then funded a pro rebrand once the model was proven.

• Automate customer wins with domain-specific AI. JackAI turns guide photos into website updates, social posts and CRM emails without human effort. Look for analogous workflows to own in your vertical.

• Obsess over customer success to slash churn. Guidesly’s 0.5 % annual churn stems from hands-on best-practice coaching; invest here before pure growth hacks.

• Sell founder-led first. “Eat what you hunt” outreach validated demand before paid ads; direct calls teach you the real objections.

• Choose initial geos for year-round revenue. Florida charters fish 365 days and gross seven figures, beating seasonal Montana rivers. Start where unit economics are strongest.

• Seek brutal expert feedback early. A tough AI investor told David “you don’t know it,” prompting a full technical reboot that became a moat; invite hard critiques.

• Scale only after the platform is complete. He finished SaaS, marketplace, and AI layers before pouring dollars into marketing, ensuring capacity matched demand.

• Build for legacy, not just exit. A mission that matters—to improve working guides’ livelihoods—magnetizes talent, investors and customers for the long haul.

Listen to David’s interview on YouTube, Spotify, or Apple Podcasts.

• David’s fly-fishing pain point that sparked the idea (guides “get screwed”)

• Tech tailwinds (Stripe, React Native, vertical SaaS) that made the model viable

• The strict “no-asshole” rule for teammates and investors

• Discovering a $50B market and deciding to fund-raise fast to win it

• Hiring only people who treat outdoor guiding as a life craft

• Building a marketplace and vertical-SaaS platform in parallel

• Why Florida’s year-round charters became the launch beachhead

• Founder-led sales that onboarded 1.6 K+ SaaS guides

• “Guide happiness” and the 0.5 % annual churn superpower

• Winning 43North and how the accelerator turbo-charged growth

• Spreading to new verticals and why vertical-AI gives a durable moat

• Launching Guidesly Pro and the company’s first brand push

• Value-add investors: how Yeti Capital’s “brand whisperer” came aboard

• JackAI: zero-click content, CRM and Google posts from a single photo

• Scaling a 20-person AI team with heavy Amazon support

• Legacy over exits: aiming for a Yeti-sized, industry-changing outcome

Listen to David’s interview on YouTube, Spotify, or Apple Podcasts.

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna