Jonathan Brickman

Our latest edition of GTM Navigator is live! We are thrilled to have Riya Grover, Co-Founder & CEO of portfolio company, Sequence, join us to dive into the world of billing & pricing. In this episode, you'll learn how to select the right billing vendor, explore emerging pricing trends, and get tips on preparing for pricing changes. Huge thanks to Riya for sharing her valuable expertise with us. Tune in using the link in the comments below!

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How will tariffs impact 2025 lower middle market M&A, diligence processes, multiples? We don't have a crystal ball either, but we interviewed a few lower middle market bankers who are actively working with affected business owners and we shared the writeup today on the Axial blog. + due diligence has changed rapidly and there are new checklists already built around this topic. Owners be ready for this. + LOIs are breaking / getting pushed out. Hopefully yesterday's announcement at least provides clarity. Markets prefer "bad news" to open-ended uncertainty. + Government Services is out of favor. Careful contrarians, this is your moment. Full write-up link is in the comments.

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Ready to elevate your fundraising game? Fundraising is not luck. It is a process. The best founders treat raising capital like a high-performing sales process. Clear targeting, disciplined outreach, and strong follow-through make the difference. It starts with building the right investor list. Focus on VCs who match your stage, sector, and check size before you ever send a deck. Want the step-by-step playbook? Read our latest VC Unfiltered article! Link in comments👇 #startup #fundraising #venturecapital

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Every is launching Payroll for startups — a payroll platform built specifically for tech startups, with compliance at its core. Startup founders aren’t payroll experts — but the IRS doesn’t care. Founders pay ~$6 billion every year in payroll-related fines. Every fixes this by doing manual compliance reviews before submitting payroll taxes. Since launch, Every has processed ~$60M in payroll payments with $0 in customer fines. Founders can now: - Hire compliantly in all 50 states and 200+ countries - Automate state tax registration and compliance - Offer competitive, tech-specific benefits to protect runway - Get expert support at every step Every was founded by Rajeev Behera after learning the hard way how costly payroll mistakes can be at a fast-growing startup. Now, Every helps founders hire and scale with confidence, without risking fines or delays. Congrats to the team on the launch! https://lnkd.in/gANVpViT

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Living at the dawn of a technological shift is exhilarating. Agentic Commerce -- AI agents searching, evaluating, and transacting on behalf of humans -- is a clear vision, but the 'how' is literally being built right now. Last week we had the joy of dining with an exceptional group of founders and executives building that future. Over dinner, several themes stood out. 🧨𝐁𝐮𝐢𝐥𝐝𝐢𝐧𝐠 𝐢𝐧𝐟𝐫𝐚𝐬𝐭𝐫𝐮𝐜𝐭𝐮𝐫𝐞 𝐭𝐨𝐝𝐚𝐲 𝐬𝐨 𝐭𝐡𝐚𝐭 𝐯𝐨𝐥𝐮𝐦𝐞 𝐜𝐚𝐧 𝐟𝐨𝐥𝐥𝐨𝐰 𝐭𝐨𝐦𝐨𝐫𝐫𝐨𝐰.  It's early, chicken and egg dynamics exist, but the infrastructure IS being built today to enable volumes and use cases to follow. 🎈𝐁𝐮𝐢𝐥𝐝 𝐰𝐢𝐭𝐡 𝐚 𝐩𝐥𝐚𝐭𝐟𝐨𝐫𝐦 𝐦𝐢𝐧𝐝𝐬𝐞𝐭.  Because the exact users and use cases will take time to emerge. Bet on B2B as the earlier adopters. 🪄𝐒𝐭𝐚𝐧𝐝𝐚𝐫𝐝𝐬 𝐚𝐫𝐞 𝐧𝐞𝐞𝐝𝐞𝐝, 𝐚𝐧𝐝 𝐰𝐞 𝐧𝐞𝐞𝐝 𝐚 𝐟𝐞𝐰 𝐛𝐢𝐠 𝐩𝐥𝐚𝐲𝐞𝐫𝐬 𝐭𝐨 𝐜𝐨𝐚𝐥𝐞𝐬𝐜𝐞 𝐚𝐫𝐨𝐮𝐧𝐝 𝐚 𝐟𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤. AP2, A2A, ATXP, ACP... all offer valuable frameworks with alternative and complementary aspects, but just like Internet 1.0, big players need to agree and implement core protocols in their tech stacks. Third-party developers have a thumb on the scale, but are necessary, not sufficient. Right now, the largest players like OpenAI, Microsoft, Google, Anthropic are not in a consensus mood. They would rather win the full-stack themselves than assign core roles like trust and identity to a third party. This will change. 🔒𝐖𝐢𝐥𝐥 the 𝐕𝐞𝐫𝐢𝐬𝐢𝐠𝐧 𝐨𝐟 𝐚𝐠𝐞𝐧𝐭𝐢𝐜 𝐩𝐚𝐲𝐦𝐞𝐧𝐭𝐬 𝐞𝐦𝐞𝐫𝐠𝐞? Through brilliant execution VERISIGN became THE arbiter of trust on the internet as the leading issuer of trust certificates (think 🔒on URLs). They had winner-take-most (for a while), and the consolidation accelerated payments on the internet. 💳𝐓𝐫𝐮𝐬𝐭 𝐢𝐬 𝐞𝐯𝐞𝐫𝐲𝐭𝐡𝐢𝐧𝐠 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮'𝐫𝐞 𝐝𝐞𝐥𝐞𝐠𝐚𝐭𝐢𝐧𝐠 𝐚𝐮𝐭𝐡𝐨𝐫𝐢𝐭𝐲. It's not easy to earn -- neither for incumbents with a track record (invariably mixed) nor startups with no track record. But trust is not all or nothing. Solutions will also need to lower the need for trust -- cap risk, clarify dispute handling and revocation, etc. 🪙𝐀𝐜𝐭𝐢𝐯𝐚𝐭𝐢𝐧𝐠 𝐭𝐡𝐞 𝐝𝐨𝐫𝐦𝐚𝐧𝐭 𝐱402 𝐩𝐫𝐨𝐭𝐨𝐜𝐨𝐥 𝐢𝐬 𝐚 𝐠𝐨𝐨𝐝 𝐬𝐭𝐚𝐫𝐭, 𝐛𝐮𝐭 𝐥𝐢𝐭𝐞𝐫𝐚𝐥𝐥𝐲 𝐞𝐯𝐞𝐫𝐲𝐭𝐡𝐢𝐧𝐠 𝐞𝐥𝐬𝐞 𝐧𝐞𝐞𝐝𝐬 𝐭𝐨 be 𝐛𝐮𝐢𝐥𝐭. Founders at the table were building the infrastructure for wallets, checkout, security, identity, intent verification, and more. A big thanks to my partner Abdul Abdirahman, our friend and co-host Vivek Krishnamurthy (Commerce Ventures), and to everyone for the great conversation. And to Blue Hill for one of my best dinners of 2025! F-Prime Mitchell Jones Ayal Karmi 🔵 Sean Neville Louis Amira Arjun Bhargava Robin Gandhi Donald Gossen Alfonso Gómez-Jordana Mañas Akash Desai Chris Blackburn Andrew Hungate Michael Duane Teddy Riker Randall Davies

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Contractors must understand the critical role of SEO in attracting clients. Many underestimate that a well-optimized website can drive organic leads and compare favorably against competition. Improving visibility can mean the difference between landing a project and being overlooked entirely. For example, companies successfully targeting local keywords have experienced significant increases in inquiries. They gain visibility in search engines, affecting their bottom line positively. The takeaway is clear: investing time in SEO translates to long-term benefits. By optimizing your website, you can create a more compelling online presence that resonates with potential customers and generates sustained engagement over time. What strategies have you implemented to enhance your SEO efforts? Share your insights. #SEO #Contractors #DigitalMarketing #LeadGeneration #BusinessGrowth https://lnkd.in/g2AxB-Nx Growth Hackers

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I’ve said it before, and I’ll say it again, investors buy performance, not potential. When we evaluate franchise brands, we don’t start with the story or the tech stack. We start with unit-level profitability. That’s the foundation for scale, validation, and enterprise value. In my new Forbes article, I break down the key metrics investors look for and why sustainable unit economics always win over flashy growth. 🔗 https://lnkd.in/e6uwkjpx Visit Boxwood Partners: https://lnkd.in/eWPtbT7q #Franchising #PrivateEquity #MergersAndAcquisitions #BoxwoodPartners

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Let’s talk about concrete agentic worklow and one of our most successful use cases! Issuing or responding to RFPs can create business opportunities or waste time and money. While we don’t believe tomorrow’s discussions between vendors and buyers will be entirely agent-to-agent, they will undoubtedly be highly automated. Each company, on both sides, must find a way to incorporate creativity into their win-win game plan. For many teams, proposal work has become highly admin-driven and a bottleneck. Requirements multiply. Documents pile up. Accuracy is critical, yet the process remains slow, manual, and inconsistent.   That’s precisely why at Sia, we built Proposal Drafting Agent, to plug that leak, streamline the process, and help teams win more, smarter. It's our AI-driven solution designed to simplify one of the most demanding parts of the commercial cycle: navigating and responding to complex RFPs.   Proposal Drafting Agent changes the equation.    By applying advanced language models to incoming RFPs and internal knowledge, the platform automatically analyzes requirements, finds the right supporting material, flags gaps, and produces a structured draft for teams to refine. It's fast, traceable, and designed for collaboration across proposal, business, and legal teams.   Less time searching, more time winning.    Discover our Agent Store in the comments 👇   #AI #AIagent #RFP Adrien GRIMAL Sia AI

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Family-owned businesses often face unique challenges when raising capital, and Licorne Gulf Holding offers strategies that address these hurdles effectively. By focusing on building strong relationships and leveraging their extensive network, they help family businesses access the capital necessary for growth. Emphasizing transparent communication and long-term planning, these strategies ensure that businesses not only secure funding but also maintain their core values. How can such businesses balance tradition with innovation to stay competitive? The answer lies in a strategic approach that respects the legacy while embracing new opportunities. This balance is crucial for sustaining growth and ensuring the long-term success of family enterprises. #FamilyBusiness #CapitalRaising #Strategy #licornegulf

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The DSG Consumer Partners x GobbleCube Qcom playbook session recording is live on YouTube. Highlights from the session include: Hyperlocal Growth Strategies: Detailed insights on how pin-code level planning drives disproportionate growth. Dedicated Product Development: Best practices for creating products optimized for Q-commerce environments. Strategic Account Management: Methods for effectively partnering with category and account managers to accelerate category scaling. Metrics That Matter: Key performance indicators essential for Q-commerce success, including velocity, fill-rate, and dark-store strategies. This session is especially useful for: Founders and brand leaders aiming for rapid scale through Q-commerce. Marketing and product development teams adapting to changing consumer behaviors. Special thanks again to Manas Gupta Srikumar Nair, Pankaj Goyal, Abhishek Agarwal, Akash Sharma, Utkarsh Gurav, Kiran Shah, Smitkumar Raval, Vinay Kothari, Raksha Kothari and the GobbleCube and DSG Consumer Partners teams. Link to the You tube session in first comment. Deepak Shahdadpuri Pooja Shirali Sameer Mehta Leong Hein Hun Urmit Shah Tushna Marolia Aditya Gogri Varun Parekh Tavishi Jatrele Rohan Shah We welcome your feedback and look forward to your questions.

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🚀 𝗩𝗖 𝗦𝘁𝗮𝗿𝘁𝘂𝗽 𝗦𝗲𝗹𝗲𝗰𝘁𝗶𝗼𝗻 — 𝗧𝗵𝗲 𝗝𝗼𝗰𝗸𝗲𝘆, 𝘁𝗵𝗲 𝗛𝗼𝗿𝘀𝗲, 𝗮𝗻𝗱 𝘁𝗵𝗲 𝗢𝗱𝗱𝘀 📑 𝘋𝘰𝘸𝘯𝘭𝘰𝘢𝘥 𝘔&𝘈 𝘗𝘳𝘰𝘮𝘱𝘵 𝘗𝘢𝘤𝘬 👉 https://lnkd.in/gvgqNTXe VCs know: the hardest part isn’t sourcing deals, it’s choosing the right ones. Here’s what the data tells us from a Midwest seed investor screening 8,000+ startups: 🔍 𝗪𝗵𝗮𝘁 𝗿𝗲𝗮𝗹𝗹𝘆 𝗺𝗮𝘁𝘁𝗲𝗿𝘀: 1️⃣ 𝗧𝗵𝗲 𝗝𝗼𝗰𝗸𝗲𝘆 𝘃𝘀. 𝗧𝗵𝗲 𝗛𝗼𝗿𝘀𝗲 • Early wins (raising $1M+) are driven by the team. • Big outcomes ($10M+ raised, survival) hinge on market and product. • Translation: teams open the first doors, but business fundamentals drive scale. 2️⃣ 𝗧𝗵𝗲 𝗢𝗱𝗱𝘀 • Out of all startups screened, ~30% raised at least $1M, but only ~10% crossed $10M. • Screening works — the VC’s analyzed companies outperformed the rest. • Still, noise is high: most investments don’t hit outsized returns. 3️⃣ 𝗧𝗵𝗲 𝗙𝗼𝘂𝗿 𝗟𝗲𝘃𝗲𝗿𝘀 When scoring deals, this VC weighed: • Team • Market Size & Competition • Product & Innovation • Exit / Growth potential The mix predicts different outcomes. Teams matter early. Markets and products matter late. Strong scores across both? That’s where the real winners come from. 4️⃣ 𝗧𝗵𝗲 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆 VC selection is far from perfect. But structured screening, even at pre-seed, improves odds. The best investors balance conviction in founders with hard-nosed assessments of markets and products. Credit: Jang & Kaplan (2025) #VentureCapital #PrivateEquity #Finance Investment #FinancialServices — 💰 𝗠&𝗔 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀 - https://lnkd.in/gsvG2eDh  📊 𝗜𝗕 𝗗𝗲𝗰𝗸𝘀 𝗗𝗮𝘁𝗮𝗯𝗮𝘀𝗲 - https://lnkd.in/gJEGnBC7  📚 𝗣𝗿𝗶𝘃𝗮𝘁𝗲 𝗘𝗾𝘂𝗶𝘁𝘆 𝗖𝗼𝘂𝗿𝘀𝗲 - https://lnkd.in/gNNZBude —

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Vision alone won’t build your company. Eric Clarke, Managing Director of our Outsourced CFO practice, shares how to align growth + funding, raise with purpose, protect your timeline, plan for the unexpected, and manage your cap table. Build with intention—investors will notice. 🔗 #StartupGrowth #FundingStrategy   Evergreen Advisors’ Outsourced CFO team is your partner in building a financial strategy that supports every stage of growth. We help founders connect the dots between vision, execution, and funding—so you can raise confidently, manage wisely, and stay focused on building the business you set out to create. Read more: https://lnkd.in/ejtq-uR3

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📊 Metrics That Shape Deals It’s not just about revenue and EBITDA. This one-pager highlights key metrics buyers use to evaluate a business—ones that spark interest, influence value, or raise red flags. Make sure you understand them before you're on the other side of the table. 👇 Preview it here before it drops in tomorrow’s edition of M&A Mindset. Want more clear, no-fluff M&A insights like this? Subscribe here: https://lnkd.in/geSRPz4X

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Follow for a free guide on owning more businesses with other people’s money! Smart business buyers and real estate investors leverage OPM (Other People’s Money) to acquire assets without using their own capital. By structuring deals creatively—using seller financing, partnerships, and investor funding—you can expand your portfolio while minimizing risk. Success isn’t about how much money you have; it’s about how well you use resources. Learn the strategies top entrepreneurs use to buy businesses and properties without breaking the bank!

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