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Between the Lines Newsletter

You Made This.

What started as years of small-group “bitch sessions” among executives struggling to reach and serve small businesses eventually sparked the creation of the B2SMB Institute. In this reflection on eight years of growth, Dave Walker traces how a fragmented group of leaders selling to SMBs—often working in isolation—came together to form a shared center of gravity for the B2SMB profession. From the first gathering at Chicago’s 1871 incubator in 2017 to a global community of thousands today, the Institute has evolved into a hub for peer wisdom, collaboration, and shared playbooks. The message to the community is simple: the Institute didn’t create the profession—it recognized it. And the people who showed up, shared ideas, and built together are the reason it exists.

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March 10, 2026
Between the Lines Newsletter

It’s Not a You Thing.

It’s not a you thing. It’s a WE problem. From collapsing search and shrinking email performance to AI confusion and rising CAC pressure, leaders across the B2SMB market are facing the same challenges—alone. In this issue of Between the Lines, we explore the cost of isolation, the myth of “figure it out yourself” leadership, and why structured peer connection may be the intervention we need. Because the problems are shared. And the solutions should be, too.

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February 26, 2026
Between the Lines Newsletter

Claude’s Wishful Thinking

The more you work with AI, the less you fear it. In a live exchange, Claude admitted its limits—accuracy gaps, governance failures, and “wishful thinking” in its own value assessment. That moment didn’t spark panic. It sparked clarity. AI is not an oracle or a Terminator. It’s a tool—powerful, evolving, and deeply dependent on human structure, judgment, and governance. Fear thrives at a distance. Understanding happens up close.

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February 19, 2026
Between the Lines Newsletter

It’s Payback Time

Acquisition channels didn’t just get expensive — they broke. Twenty-month paybacks, 60%+ CAC inflation, expansion costs rising, and working capital locked inside growth have turned scale into a liability instead of an advantage. This isn’t a marketing execution problem. It’s infrastructure failure. In this issue of Between the Lines, Dave Walker lays out the math, the governance reckoning facing CEOs and CFOs, and why partnership-led growth may be the only structural escape from a system that no longer works.

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February 11, 2026
Between the Lines Newsletter

The River Is Burning

In 1969, the Cuyahoga River caught fire after decades of pollution — a breaking point that led to the Clean Water Act. Today, our business communication channels are burning for the same reason. Email deliverability is collapsing. Organic search traffic is evaporating. Social reach is shrinking. AI hasn’t destroyed the system — we’ve flooded it. In this issue of Between the Lines, Dave Walker argues that the B2SMB go-to-market crisis isn’t a technology failure. It’s a behavioral one. And unless we stop dumping volume into already saturated channels, the river will keep burning.

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February 4, 2026
Between the Lines Newsletter

Between the Lines: The 2026 Momentum Report

In Part 1 of his three-part series on the $2.5 trillion small business marketplace, Dave Walker examines how SMBs are moving faster than traditional B2SMB sellers can keep up. In 2025, small businesses quietly adopted AI at record rates, launched new businesses in unprecedented numbers, and prioritized payments innovation and embedded finance as essential. Meanwhile, tax law changes like the expanded Section 179 deduction created immediate opportunities for capital investment. Walker argues that growth now favors sellers who solve practical problems quickly, offer seamless financial and operational tools, and lead with tangible outcomes, not just features.

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February 2, 2026
Between the Lines Newsletter

The Forecaster’s Dilemma

In The Forecaster’s Dilemma, Dave Walker explores why traditional quarterly forecasting is failing in today’s rapidly evolving B2SMB market. Using HubSpot, ADP, and Shopify as examples, he illustrates that models built on historical trends and predictable variables break when AI, partnerships, and shifting market structures redefine what customers value. The companies that succeed aren’t trying to predict the next quarter—they’re forecasting market direction 3–5 years out, making strategic bets on trends, and guiding quarters conservatively. Walker argues that in 2026, forecasting the market—not the quarter—is the only approach that creates sustainable growth.

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January 28, 2026
Between the Lines Newsletter

80% of B2SMB Partnerships Fail. Is Yours?

In 80% of B2SMB Partnerships Fail. Is Yours?, Dave Walker explores why the majority of B2SMB partnerships falter before delivering real value. Based on surveys and peer discussions with executives from companies like Zoho, Equifax, Intuit, and OpenPhone, he identifies three key challenges: (1) no consistent way to measure partnership success, (2) the time-intensive process of finding and closing with qualified partners, and (3) the inability to distinguish strategic alignment from tactical fit. Walker argues that partnerships are no longer optional—they’re essential for resource leverage, competitive advantage, and opportunity acceleration. The solution? Curated introductions, shared frameworks, and peer learning via the B2SMBI Partners Circle, designed to pre-vet partners, benchmark success, and focus on long-term strategic alignment.

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January 21, 2026
Between the Lines Newsletter

Part 3: Is 2026 Hiding in Plain Sight?

In Is 2026 Hiding in Plain Sight?, Dave Walker closes his three-part series on the $2.5 trillion small business market by highlighting the biggest unmet SMB needs that will define 2026. From 46% of SMBs suffering cyberattacks with only 17% insured, to 42% being hurt by tariffs without planning tools, and 70 million gig workers underserved by W-2-optimized HR platforms, Walker identifies massive opportunity gaps. He argues that winning B2SMB solutions will not be better versions of existing tools—they will create entirely new categories: simple, integrated cybersecurity for SMBs, tariff impact and supply chain scenario planning, and unified platforms for managing W-2 and gig workers alike. The key pattern: SMBs are moving faster than vendors, and the companies that recognize and act on these gaps will thrive in 2026.

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January 8, 2026
Between the Lines Newsletter

Part 2: Is the Middle Disappearing?

In Is the Middle Disappearing?, Dave Walker explores the growing divide in the $2.5 trillion B2SMB market. In 2025, platform consolidators like Salesforce and Intuit built massive all-in-one “battleships,” while vertical specialists such as Toast, ServiceTitan, and Procore became nimble category dominators. Caught in the middle are mid-size generalists—companies like Gusto, LegalZoom, and Indeed—too small to consolidate and too broad to own a vertical. Walker warns that horizontal players face slowing growth and pricing pressure, and must choose: punch up to compete with the giants, punch down to become a specialist, or merge/acquire. The middle ground is shrinking, and 2026 will favor those who deliver the right features for SMBs, not the most features.

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January 7, 2026
Between the Lines Newsletter

Part 1: Are Small Businesses Moving Faster Than Us?

In Are Small Businesses Moving Faster Than Us?, Dave Walker examines how SMBs outpaced B2SMB vendors in 2025, reshaping a $2.5 trillion market. Small businesses quietly adopted AI at unprecedented rates, optimized payments, and integrated embedded finance as essential operations tools. New business formations surged, creating a digitally fluent generation of buyers who expect frictionless onboarding and instant value. Meanwhile, tax incentives like Section 179 offer SMBs tangible financial outcomes that most vendors fail to leverage in their sales strategies. Walker warns B2SMB sellers: SMBs are moving faster than traditional playbooks anticipate, and success in 2026 will favor those who deliver solutions that save time, simplify operations, and reduce friction in immediate, measurable ways.

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January 6, 2026
Between the Lines Newsletter

Partnership Theater vs. Business Reality

In Are Small Businesses Moving Faster Than Us?, Dave Walker examines how SMBs outpaced B2SMB vendors in 2025, reshaping a $2.5 trillion market. Small businesses quietly adopted AI at unprecedented rates, optimized payments, and integrated embedded finance as essential operations tools. New business formations surged, creating a digitally fluent generation of buyers who expect frictionless onboarding and instant value. Meanwhile, tax incentives like Section 179 offer SMBs tangible financial outcomes that most vendors fail to leverage in their sales strategies. Walker warns B2SMB sellers: SMBs are moving faster than traditional playbooks anticipate, and success in 2026 will favor those who deliver solutions that save time, simplify operations, and reduce friction in immediate, measurable ways.

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December 17, 2025
Between the Lines Newsletter

Part 3: Future-Proofing Your B2SMB Career

In Future-Proofing Your B2SMB Career, Dave Walker outlines the massive opportunity arising from the AI implementation gap in small businesses. While most SMBs are eager to adopt AI, fewer than 20% use it effectively, creating demand for skilled professionals who can bridge the gap. Walker highlights three emerging roles—AI Implementation Consultant, SMB Success Manager 2.0, and AI-Powered Product Marketer—and provides a detailed 12-month roadmap to develop skills, build a portfolio, and scale impact. He also explores entrepreneurial and internal transformation paths, emphasizing service-augmented models, done-for-you and done-with-you approaches, and the value of outcome-driven implementation. The key takeaway: acting now to establish AI implementation expertise will create career leverage and long-term market advantage in the rapidly evolving B2SMB landscape.

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December 3, 2025
Between the Lines Newsletter

The 2026 B2SMB Career Guide – A Special 3-Part Between2Bs Series

In Thriving in the Transformed B2SMB Market, Dave Walker explores how the Business-to-Small-Business landscape is rapidly shifting due to AI, solopreneur growth, and economic disruption. He highlights the emerging career opportunities for B2SMB professionals who can bridge the AI implementation gap, providing hands-on guidance and strategic support to SMBs. Walker emphasizes the importance of treating AI as a productivity co-pilot, understanding solopreneur needs, and positioning oneself as an intrapreneur or implementation specialist. The article provides actionable 90-day steps—ranging from skill-building and certification to portfolio creation and pilot projects—helping professionals make themselves indispensable in the evolving market. The key message: B2SMB careers now reward empathy, technical literacy, and initiative.

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November 11, 2025
Between the Lines Newsletter

Is AI Getting Impatient?

In Is AI Getting Impatient?, Dave Walker explores the rapid evolution of AI-native companies in the B2SMB space, likening the surge to a Cambrian Explosion of business software. From autonomous financial systems like Digits to AI-powered sales reps like Artisan AI, Walker highlights how these emerging platforms are rewriting the rules for SMBs. The article emphasizes that traditional software “improvements” are no longer enough—success now demands building AI-first, unified, and industry-specific solutions. B2SMB leaders are challenged to shift from incremental upgrades to fundamentally new approaches, leveraging AI to automate, unify, and drive outcomes across finance, operations, and go-to-market. Walker’s key takeaway: AI isn’t waiting, and those who adapt first will define the next decade of B2SMB leadership.

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November 4, 2025
Between2Bs Podcast

The AI2SMB Playbook You’ve Been

Top SMB Tech Influencer John Lawson has thoughts on AI2SMB. From his early days showing how to tie bandanas on YouTube, to today’s bestseller, The Ultimate AI Marketing Manager, John’s surfed every major tech wave since 2000, and he’s talking why 77% of SMBs are still in their AI infancy.

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October 15, 2025
Between2Bs Podcast

A Hard Conversation About AI2SMB

Tech Pros from Vcita & AWeber reveal why 70% of small businesses feel “completely unprepared” for AI, but are they simply unprepared for the AI Big Enterprises are building for and selling to them? What if those same builders and sellers did the hard work for SMBs? Buckle up for the answers!

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September 24, 2025
Between2Bs Podcast

Escaping Death Valley: Filling the Gap Between Marketing & Sales

In this episode, Dave Walker speaks with Steve Prestidge from Centerfield about the evolving $2.5T B2SMB marketplace, the ever-growing challenge of winning, keeping and growing Small Business Customers at scale, and the ever-present “Death Valley” between enterprise marketing and sales. The conversation also touches on the importance of trust, the future of buying through comparison and deals, and how businesses can navigate the complexities of AI2SMB go-to-market.

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September 17, 2025
Between2Bs Podcast

Co-Founder of Housecall Pro on the Importance of SMB Community

HouseCall Pro’s co-Founder Roland Ligtenberg shares how building a genuine Community of local service pros transformed their platform into an essential business tool. That tool is handier than a hammer or wrench, used an average of 7.25 hours daily by 100K+ users. His pragmatic “Community-led Growth” playbook drives success via deep user connections, multiplying the power of solo-preneurs into a vibrant growth-driving customer base. He’s one of our keynote Speakers at our Sonoma Leaders’ Forum – Join us on this latest episode of the Between2Bs podcast.

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April 8, 2025
Between2Bs Podcast

Between2Bs: WSJ Best Selling Author Sangram Vajre

Join us as B2B “Top 21 Global Marketing influencer” Sangram Vajre unpacks his proven Go-To-Market (GTM) framework from his WSJ bestseller, “Move.” Drawing from his career building breakouts, including two $100M+ exits, he shares how businesses at any stage can adapt and thrive in today’s rapidly changing $2.5T B2SMB marketplace.

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March 4, 2025
Between2Bs Podcast

10 Predictions For Transforming Customer Experience In 2025

Forbes Advisor Small Business editor Bryce Colburn talks AI’s impact on SMBs, emphasizing its role as a competitive equalizer against the Big Guys. He highlights AI’s evolution from buzzword to practical tool, its potential for real personalization, and how it can enhance creativity as a “tireless teacher” that helps entrepreneurs explore and develop ideas.

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March 1, 2025
Between2Bs Podcast

Between2Bs: The New Sell Of AI – The New Sell With AI

Between2Bs Podcast: The New Sell Of AI – The New Sell With AI

Breakout AI-player Augment’s co-Founder Jordan Ritter talks to Dave Walker of B2SMBI about how his Team is building AI into the “New Sell.”

As our B2SMB marketplace explodes with new AI-based products directed at SMBs, are Sellers to Small Business applying AI to their own efforts to engage, qualify and close prospects?

We’ll explore what’s possible and what’s fast becoming must-have in a “next wave” sales environment demanding:

Hyper-personalization
Offer-customization
Rich-data contact management
And a boost of AI-generated insights

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February 5, 2025
Between2Bs Podcast

Between2Bs: NewBie-2SMBs: Member Marketplace and SMB.co

This week’s Between2Bs podcast features Cherie Edelson of Member Marketplace, whose building commerce hubs for small business groups, like ShopIowa.com, and Joe Brown of SMB.co, building a “Zillow for Small Business”, connecting SMBs looking to sell their business, and verified Buyers. Join us for insights into their innovative marketplace solutions!

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February 4, 2025
Between2Bs Podcast

Are We AI2SMB Ready? Brian Moran on the State of the Market

Brian Moran’s Small Business Edge podcast reaches 100+ countries and has engaged 100,000+ SMBs. We explore AI2SMB readiness – and apparent roadblocks – with Brian, who believes: “Enterprise AI solutions don’t fit small business realities. To move beyond early adopters, we need a playbook.” Join us for a tour of that Playbook.

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January 23, 2025
Between2Bs Podcast

Year in Review, Year to Pursue

B2SMB Institute’s CEO Dave Walker is joined by CGSO Maciek “Magic” Szczesniak to abbreviate the many hours worth of dialogue they’ve had on 2024 and 2025 in the world of Business-to-Small-Business.

Riffing off the expansive “Year in Review, Year to Pursue” now available for free download, Magic and Dave cover the waterfront of trends, developments, forecasts and more.

Sitting at the center of the Business-to-Small-Business ecosystem, they draw on the direct conversations they’ve had with B2SMB Enterprise C-Suites, Senior Marketers and Sales Execs, break-out Product Developers, SMB Influencers and Media, and more.

Highlights include:

The economy and the SMB – up, down or sideways?
The democratization of SMB “tech transformation” – can you say AI?
The throughline of 2024 into 2025 – is the Playbook written for us?
Recommendations from the recommendations – greatest hits from our many B2SMB Leader interviews in the last few months

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January 13, 2025

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