focal podcast

You have to be so much better than the incumbent if you want to have even the slightest change.This episode is a tactical masterclass on early-stage B2B sales. You’ll learn how to nail the first meeting, architect modular demos, multi‑thread like a pro, and turn proposals into “Champion Empowerment” decks that actually close. We also cover ROI modeling, executive sponsorship, outbound strategy, and the exact behaviors that separate A‑players from everyone else.Our guest is Greg Costigan leads the sales team at Performica and has built and led GTM organizations at Box, Zuora, Zenefits, LearnUp, Hone, and MindGym. He’s closed complex enterprise deals, championed award‑winning programs (e.g., Pinterest’s Brandon Hall–recognized L&D initiative), and specializes in taking startups from founder‑led sales to scalable processes.In Today’s Episode We Discuss:01:33 - Sales process is a science—ditch gut feel for repeatable rigor.04:51 - Stop skipping steps—credibility beats the ‘one‑call close’ myth.07:01 - First meeting playbook: GGGA, pre-read, ruthless prep.10:57 - Lead with a hypothesis—change the buyer’s frame (Challenger).13:32 - First-call exceptionalism: come in hot and create momentum.14:51 - Yes, demo on call one—and land a clean close.19:44 - Multi-thread fast: champion texting, exec sponsors, rule of threes.22:19 - Demo excellence: send agenda early, close BANT/MEDDICC gaps.23:59 - Modular demos: tailor admin, user, integrations to stakeholders.27:51 - End every demo with a scoping or proposal—never ambiguity.34:14 - Turn proposals into a Champion Empowerment deck that sells itself.36:54 - No exec sponsor? You’re at risk—fix it before forecasting.38:20 - Build a simple ROI model—finance will ask, be ready.54:49 - Outbound isn’t dead—SDRs matter more than ever.

Moving upmarket, the right wayWhen should a startup go from SMB to enterprise - and when should you not?I break this down with a former revenue leader at Box, SurveyMonkey, Asana, etc - Matt Harmon (ex‑Box, Asana, SurveyMonkey). We discuss the real signals for enterprise readiness, why security/compliance readiness matters, and why “we’ll build it if you buy it” kills confidence. We also compare playbooks for existing vs. new categories, the land→expand reality, and how to balance self‑serve revenue with enterprise ambitions.In Today's Episode We Discuss:1:42 Why the “go upmarket” conversation starts early4:53 Company readiness: security, compliance, SEs, forecasting shifts10:57 Signals it’s curiosity-only vs. a real enterprise opportunity16:45 “Is it someone’s KPI?” and the need for true pain/need18:36 Existing category = one path to buy (ripping/replacing)22:52 New category upmarket: shared services & proving uniqueness28:28 Land→expand and product-led reality33:08 Don’t force a model—map the customer journey first37:57 Positioning and intellectual honesty at ~$1M ARR40:00 Category creation vs. innovating in an existing one45:07 Why not to fear SMB/self-serve revenue47:15 Don’t over-index on “sell to pain” for new categories50:15 Founder advice: embrace ambiguity and EQ52:25 What great VCs do: back leaders who can hire leaders

Bootstrapping to $10M ARR was easier than raising the first $20M.This episode is a masterclass in founder decision-making: choosing (and parting with) co-founders, bootstrapping to real revenue, then raising at scale - without losing the plot. Expect frank takes on titles, burn, investor selection, and the moral weight of taking other people’s money.Duncan Weatherston is the co-founder and CEO of Smile Digital Health, a leading healthcare data platform company. He and his team bootstrapped to ~$10M ARR before raising a $20M Series A, and are now well past $50M in ARR.01:40 - Why start with co-founders vs going solo in healthcare SaaS06:27 - How to vet co-founders: proof of execution over chemistry06:58 - The #1 mistake: trusting claims without validating capability09:39 - Early-stage stars rarely scale—how roles must evolve12:25 - Title inflation trap: why early VP labels backfire later12:47 - Be mercenary with misfits: fairness to the team > feelings16:56 - Create IC ladders: don’t “promote” top engineers into management18:27 - Founder vesting: avoid dead equity with 5–6 year schedules19:46 - Why they bootstrapped first: expertise, low burn, paying customers22:40 - Would he raise earlier today? Services-led product tradeoffs25:47 - The $20M decision: buyouts, tailwinds, and scaling delivery34:04 - Taking VC creates a moral obligation—here’s what that means36:56 - 2021 mistake: “spend aggressively” and adapting too slowly45:59 - The do-over: fix org design, roles, and accountability sooner46:25 - Popular advice he rejects: don’t contort your playbook to fads48:41 - PMF obsession: identify your repeatable sales unit before scaling51:03 - Best investor advice: hire actual A-players, not just roles

When every YC batchmate wanted their product and investors threw money at them, Arc made the unthinkable decision - abandon the business. Learn the framework for identifying false product-market fit that saved Arc from the fate of their now-struggling competitors.Basile Senesi is the Chief Revenue Officer at Arc, the financial operating system for growth companies. He's built multiple YC companies including Phonebox (raised $500M+), is a prolific angel investor, and owns Chateau Pavo winery in Sonoma.In Today's Episode We Discuss:02:17 - How Arc originated $100M in loans then killed the product07:25 - The warning signs that made them abandon massive revenue growth10:49 - Why unit economics matter more than investor expectations14:16 - How to convince investors to kill your fastest-growing product16:38 - Pivoting from lending to cash management during market chaos19:05 - Why do the hard thing first in fintech22:14 - Everything is a funnel: validating ideas without building27:34 - Building operating models before you have revenue34:50 - Why startups need pessimistic salespeople37:00 - How to know when you're building the wrong business40:14 - Not all revenue is created equal in venture43:11 - Hire for the long haul, not the next milestone46:54 - Tactics equal strategy in early-stage startups50:49 - Learning what not to do is your competitive advantage

Don Muir turned down his dream job at Apollo to build the AI-powered bank Arc.This episode goes through the exact playbook the former BCG consultant and private equity investor used to de-risk his leap into entrepreneurship - including his 3-point checklist that allowed him to say no to Apollo. Don shares hard-won lessons about finding product-market fit, recruiting world-class talent, and why it took 190 rejections to get to his first 10 customers.Don Muir is the co-founder and CEO of Arc, a zero-asset commercial bank powered by AI that offers intelligent capital management and private credit to ambitious businesses. To date, Arc has raised over $180M in debt and equity.In Today's Episode We Discuss:01:30 - Why I chose debt over equity and existing markets over new ones04:10 - The bottoms-up approach to finding your unique right to win08:44 - From crowdfunding communities to non-dilutive capital: 4 pivots to product-market fit11:42 - Execution over innovation: Why first-time founders shouldn't reinvent the wheel14:14 - The 3-point checklist before rejecting Apollo's offer16:26 - Getting 10 CEO signatures with just a Stanford email address21:49 - 190 rejections, then 10 straight wins: The LOI breakthrough moment23:29 - Finding fast-moving waters: When to pivot vs. persevere25:28 - The Stanford.edu email hack that opened CEO doors32:25 - Why technical co-founder pedigree is overrated (but VCs disagree)38:07 - How one $100k check turned hundreds of "no's" into "yes's"42:32 - The sleepless nights that forced the Apollo phone call45:59 - When your biggest rejection becomes your largest partner49:41 - Why the "safe path" is actually the riskiest choice52:55 - The venture capital myth: Why most startups don't need VC money

Anis Bennaceur, Co-founder & CEO of Attention, shares invaluable insights from his journey as a second-time founder. He reveals the 'Triangle of Talent,' why most startups fail in hiring, and how to spot candidates with founder-like qualities. Anis highlights innovative interview techniques, including the midnight email test and the anti-selling strategy to filter out non-committed candidates. The discussion emphasizes that true stars can't be trained and why work-life balance might hinder startup success.

Russ Thau, a seasoned revenue leader with experience at companies like Intercom and Box, shares insights on improving sales rep productivity. He emphasizes that time management is crucial and discusses the importance of preparation and follow-up in sales calls. Thau reveals valuable strategies for scaling revenue and hiring effective sales teams, stressing that reps are human beings, not just metrics. He also tackles the pitfalls of conversion rates and offers a framework for founders to enhance their sales processes.

What got you here won't get you there - the brutal truth about scaling from $1M to $50M in revenue.If you keep doing what you were doing to get to $1M ARR, you won’t get to $3M ARR. What got you to $3M won’t get you to $10M, what got you to $10M won’t get you to $20M, and so on. The hard truth about rocket ship startup growth is that you have to reinvent yourself at every major revenue milestone you reach. But unfortunately, most founders can't do it. They cling to what worked, scale what's broken, and wonder why growth stalls.In this episode, I sit down with Russ Thau, a former founder and seasoned revenue leader specializing in scaling companies from $1M to $50M in revenue, to discuss what you have to do when on the Sales side to reach $50M+ in revenue as fast as possible.Russ has has scaled revenue from single digit millions to $150M+ and two IPOs at companies such as Intercom, Box,  and Envoy, and he's also advised companies like Airtable and LaunchDarkly since they were sub-$1M in revenue.In Today's Episode We Discuss:02:02 - Why being a good salesperson is actually bad for getting to $1M revenue04:31 - The counterintuitive shift from "do everything" to "go extremely narrow" at $1M07:34 - How to identify role model customers that create herd momentum11:16 - The dangerous TAM trap: why you DON'T need a billion-dollar market early on16:48 - When to stop narrowing and start widening your ICP at $3M+20:33 - The "premature scaling" mistake that kills momentum at $3M27:54 - Why the bowling pin strategy beats boiling the ocean from $3M to $10M32:01 - When "good chaos" signals it's time to implement real processes38:22 - The 5 critical metrics every revenue leader needs at $10M44:08 - How Box bet the entire company on enterprise at $20M (and won)50:52 - The 3 types of startup employees - and why nobody spans all three54:08 - Where to find entrepreneurial salespeople (hint: failed startups)1:01:08 - When to start "sprinkling in" process-oriented people vs entrepreneurs1:04:59 - The founder-to-sales-leader handoff: optimal timing and structure1:11:30 - Why agility beats everything else in startup revenue growth

How to nail partnerships from Day 1Get insights into the counterintuitive playbook that defies conventional wisdom about when startups should pursue partnerships with Natasha Ratanshi-Stein, Founder and CEO Surfboard, who nailed partnerships as their main GTM channel almost from Day 1 and eventually generated 55% of revenue through partners. Surfboard is a workforce management platform for customer service teams. After raising a $5 million seed round in 2022, they successfully exited to Dialpad in 2024 - a company they started engaging with as a partner first.In Today's Episode We Discuss:01:17 - Why partnerships before customers isn't crazy02:20 - Which partners actually move the needle for early startups?04:55 - How to convince big partners when you have zero revenue08:20 - The exact story framework that opens partnership doors10:17 - From informal to 20% revenue share: partnership evolution13:37 - Critical enablement mistakes that kill partnerships19:38 - Running partnership meetings that actually drive revenue21:41 - Do your partners even watch your enablement videos?22:39 - The Series B to pre-IPO partnership sweet spot27:17 - Early signals a partnership will fail29:31 - Negotiating partnership agreements: what founders miss33:53 - Why paying marketplace listing fees is usually worthless37:38 - When partnerships generated 55% of total revenue39:40 - The hidden partnership integration tax nobody discusses40:30 - Launching 20 partnerships, 5 worked43:29 - The dangerous 20% rule for partnership dependency45:21 - When Zendesk bought our competitor: partnership nightmare52:18 - The one hiring mistake every founder makes

Guillaume Jacquet, co-founder and CEO of Vasco, brings expertise from scaling B2B startups through the crucial $1M-$10M journey. He discusses the perils of relying on 'founder magic' and the necessity of specialization in hiring. Jacques reveals why customer success should precede sales and the importance of a structured sales pipeline. He highlights that 80% of growth success is science, not magic, insisting that startups should avoid reinventing the wheel to achieve predictable outcomes.