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I work with founders and executives who have reached a point where their current way of…
Articles by Kevin
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The "Should" Trap: Why Your Need for Control is Killing Your Results
The "Should" Trap: Why Your Need for Control is Killing Your Results
We’ve all been there—or worked for someone who was. It’s that tight grip on the wheel: the micromanaging, the daily…
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The Transformative Benefits of Adaptive Leadership
The Transformative Benefits of Adaptive Leadership
"Adaptive leadership is about taking a step back to see the bigger picture and understand the underlying issues, rather…
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Altering what's possible for your future
Altering what's possible for your future
Four Steps to Enabling Transformational Growth We've all heard about business transformation and its critical…
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This statement from Matt Abrahams is one of my all-time favorite ways of communicating
This statement from Matt Abrahams is one of my all-time favorite ways of communicating
What, so what, now what. When I read LinkedIn posts, I see a lot of "what," but not the "so what," and very little "now…
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Non-Attachment: A Leader's Guide to Sustainable Success
Non-Attachment: A Leader's Guide to Sustainable Success
Many of us have worked for or with someone who needed to control every aspect of the work and the business…
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Alignment between Mission, Vision, Values, and Purpose?
Alignment between Mission, Vision, Values, and Purpose?
What is your life's Purpose? Is it aligned with your company's Mission, Vision, and Values? As an advisor and Executive…
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The Transformative Benefits of Adaptive Leadership
The Transformative Benefits of Adaptive Leadership
"Adaptive leadership is about taking a step back to see the bigger picture and understand the underlying issues, rather…
2 Comments -
Are you ready to enable Transformational Growth?
Are you ready to enable Transformational Growth?
Four Steps to Enabling Transformational Growth We've all heard about business transformation and its critical…
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Quit vs Grit: How strategic quitting can lead to greater success, well-being, and innovation
Quit vs Grit: How strategic quitting can lead to greater success, well-being, and innovation
Quit vs Grit: How strategic quitting can lead to greater success, well-being, and innovation. Have you heard the trope,…
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Personal Transformation through Authenticity, Integrity, Purpose and Power
Personal Transformation through Authenticity, Integrity, Purpose and Power
How to Achieve Personal Transformation with Authenticity, Integrity, Purpose and Power Since becoming an ICF accredited…
4 Comments
Activity
5K followers
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Kevin McKeand reposted thisKevin McKeand reposted this🚀 Startups don’t just need faster coding, they need faster product delivery. We compared Cursor and Flatlogic Generator from a business perspective: 💻 Cursor → accelerates developer productivity inside the IDE ⚙️ Flatlogic Generator → generates full-stack business apps with backend, database, APIs, auth, and deployment structure included The key difference is speed to production, not just speed to code. For founders and product teams, the winning AI tool is the one that reduces development time and technical overhead at scale. Read the full comparison: https://lnkd.in/dmxnq8zd #Startups #AI #SaaS #ProductDevelopment #WebDevelopment #VibeCoding #CursorAI #Automation #Founder #TechInnovationCursor vs Flatlogic Generator: Best Tool for Startups & SMBs in 2026Cursor vs Flatlogic Generator: Best Tool for Startups & SMBs in 2026
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Kevin McKeand reposted thisKevin McKeand reposted thisOver the past year, we noticed something at Flatlogic: without even realizing it, we've been doing a lot of AI projects and integrations for various clients. We built AI systems for things like visual inspections, weather predictions, analyzing transcripts, pulling data from documents, automating CRM and ERP systems, creating operational dashboards and, of course, building AI chatbots :) A few weeks ago I decided to pause and realized: "Wait, this isn't just occasional AI work - this has become a key part of what we do constantly and repetitively for majority of our clients". So today we're officially launching our dedicated AI Consulting Services: [Link in the first comment!] The approach is simple: Find real business problems, messy processes, and repetitive tasks. Figure out where AI can really help-not just buzzwords. Quickly create useful AI pilots that deliver immediate benefits. Please let me know what you think!
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Kevin McKeand reposted thisKevin McKeand reposted thisFor almost two years, we had the great experience at Worldsphere.ai of working with a top 1% software development company - Flatlogic. Super honest, extremely hardworking, completely dependable. It was great to have such an amazing team led by Philip Daineka. I really enjoyed our meetings and I felt like we were doing software engineering the “right way”. I still think that working with true professionals who have extensive experience in software architecture, testing, development and deployment is the BEST way to build software. And if any company is looking for a fantastic team of developers I am happy to provide a reference to Flatlogic. I think what has happened with many CEOs and founders is that, even though we know our development teams can do a better job of creating software, our minds have been hacked by the promise of agentic coding. I’ve spent most of my 44 years involved in technology in some way. From getting my Microsoft certified professional in TCP/IP at age 18 (thanks to Mario Cerrato) to having the chance to lead amazing technology teams across many countries. My number one frustration was that I couldn’t just “do it on my own”. Even though working with these teams was a great experience, my mind was always looking for “how can I just do this faster and on my own”. I guess this is the way alot of entepreneurs think - that’s why we eventually leave the corporate world and start something from scratch. And that is the crux of why vibe coding is so addictive to founders. I would imagine that for founders who are not technical (the opposite of me) it might be even more addictive. Think of it like getting a superpower that allows you to create, in 1 minute, what used to take 5 people 1 week. Let’s say that you are a doctor - how would it change your life to be able to see 100 patients in 1 minute? And actually provide a reasonable level of care? Imagine you are a a pilot - how would your job change if you could fly across the country 10 times in one morning? With the same level of safety as before. This is what founders are trying to cope with these days. In fact, next time you see an entrepreneur you should ask them how they are feeling because they are probably completely overwhelmed by agentic AI. When given a tool that can do this at such a low cost - what would hold you back from the fantasy of using it for 10 hours a day and building every app and every feature you have ever wanted to make? And I think it’s fair to say that those of us using these tools know their limitations better than anyone. We’ve run into situations where codebases have been destroyed. We’ve had to start from scratch after days of work. Some of us have seen codebases deleted. And yet - we keep doing it. But maybe it’s time to step back a bit and think about why working with a team is so valuable? It’s not just about speed is it? For software to succeed over the long term, I still believe it needs a team of humans behind it.
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Kevin McKeand shared thisI recently became a Volunteer Deputy Voter Registrar in Travis County. Not because of politics or party affiliation, but because I believe voting is part of our civic responsibility. If you’re eligible to vote, register. And when the time comes, vote. The Declaration of Independence says government derives its just powers from the consent of the governed. That idea only works if people actually participate. When a large share of the eligible population votes, the outcome is more representative of the broader public. It reflects more people, more perspectives, and a wider set of interests. Apathy is not a strategy. And telling ourselves one vote does not matter is not a good enough reason to sit out. You do not have to agree with everyone. You do not have to love every candidate or every issue. But if you are eligible, you should participate. Register. Pay attention. Vote. That is how we build a government that better reflects the people it serves.
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Kevin McKeand shared thisI spent this week at SaaStock USA 2026 as both a volunteer and an investor. I'm sharing my personal insights from the event - the overall summary is this - AI is no longer the story. It’s the baseline. I wanted to be there to support Alexander Theuma and his team, support the Austin startup community, and put myself in the room with founders, operators, and investors working through what comes after the AI inflection point. Lately I’ve been thinking a lot about Mike Maples Jr.'s framework from Pattern Breakers: inflections, insights, and ideas. The inflection has already happened. AI is here. What matters now is who turns that shift into real insights and real company-building ideas. That’s why the Founderpath stage stood out. Alex and David Umpleby curated grounded founders, not outliers with unrepeatable stories. In some cases, these were founders who spent a decade building, pivoting, and staying close to customer needs before reaching real scale and $100M+ valuations. That was far more useful than hearing polished stories about overnight success. Peter Walker shared strong data on fundraising, valuations, and Carta benchmarks. Nathan Latka was, as always, engaging, entertaining, and insightful. I was also impressed by Amanda Kahlow and what she’s building at 1mind. We talked about how younger buyers want answers and confidence without the anxiety and pressure of engaging a salesperson too early. That shift is real, and I believe products like 1mind are directionally aligned with where sales is going. Colin Nederkoorn’s talk on Customer.io also stuck with me. His point was that before the company broke through, he had to transform himself, and then help transform his team. That resonates deeply with my coaching work. Founders often want better outcomes, but the breakthrough usually starts with leadership transformation first. The biggest difference from last year? AI no longer felt novel. It felt assumed. If your product and GTM motion still don’t meaningfully incorporate AI, you’re already behind. In some categories, you’re being disintermediated. I also loved hearing Alex talk about the transformation from SaaStock to Shift, starting with Shift Europe 2026 in Barcelona. That move makes sense. Not because SaaS is dead, but because the market has changed, and strong companies adapt. Thanks to Alex and the team for letting me be part of it. Great week. Great people. Clear signals about where things are going.Customer.io Platform: Automation, Data, Content CreationCustomer.io Platform: Automation, Data, Content Creation
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Kevin McKeand shared thisGetting a tech company to its first $1M in ARR is hard. Getting from $1M to $5M is a different game altogether. As an investor, LP in a VC fund, PE-backed CEO, and C-level operator, I’ve seen firsthand that the next phase of growth usually doesn’t require more ambition. It requires founders and executive teams to evolve how they think, lead, and execute. What got a company here often won’t get it there. That’s why I launched Founder Coaching (https://lnkd.in/gbd7gKVE) - my coaching is exclusively focused on founders and their executive teams. Often my coaching is funded and encouraged by VC/PE/FO investors who want to support their portfolio founders to reach the next level of growth, not just by doing more or better, but by BEING better (ontology) I work with founders and executive teams to help them navigate the leadership shifts required for the next stage of growth — greater clarity, stronger alignment, better execution, and the adaptive capacity to lead through complexity. For founders and for investors who want to support the leaders building enterprise value, take a look at the site and schedule an assessment: https://lnkd.in/gbd7gKVE
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Kevin McKeand shared thisAdaptive leadership is the practice of mobilizing people to tackle tough challenges and thrive. In business, that means helping founders and executive teams lead effectively when the path forward is unclear, the stakes are high, and old solutions no longer work. The transformational benefits of Adaptive Leadership that I focus on in our coaching practice. https://lnkd.in/gbd7gKVE
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Kevin McKeand shared thisMost coaching doesn’t increase enterprise value. That’s the problem. 🚀 I recently built my personal coaching site with AppWizzy, and launched my coaching practice: https://lnkd.in/gbd7gKVE I bring the perspective of an investor, PE-backed CEO, and C-level operator who’s been accountable for growth, performance, and outcomes — not just conversations. 📈 I work with founders and executive teams who need to: – scale faster – lead effectively under pressure – and deliver real, measurable results For PE and VC firms: 💰 If you’re serious about driving returns, leadership quality inside your portfolio isn’t optional. It’s the lever. I work directly with founders and C-level teams to navigate the moments that determine whether value is created or destroyed. If that resonates, take a look at the site and schedule a 30-minute assessment: https://lnkd.in/gbd7gKVE
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Kevin McKeand shared thisMost coaches don’t own their platform. They rent it. Monthly fees. Platform lock-in. Payment fees. Limited control. I wanted something different. So I built my own coaching site using AppWizzy — no coding, with a database, and hosting, fully branded, and integrated with everything I need (Calendly, Stripe, LinkedIn, YouTube). No subscriptions. No middleman. Just a platform I actually built myself, and I own it. If you’re a life or executive coach thinking about building your own presence, it’s worth a look. Here’s what I built: https://lnkd.in/gbd7gKVE Founder CoachingKevin McKeand shared this🚀 Coaching Website Templates & Custom Domains are now available! We’re excited to introduce new coaching website templates, along with custom domain support, making it easier than ever for coaches and creators to launch a professional online presence. What’s new: - Ready-to-use website templates tailored for coaching businesses - Seamless custom domain integration for stronger branding - Faster time-to-launch with minimal technical setup - Built to support real-world use cases from day one This release reflects a broader shift toward simplifying website creation, helping users go live quickly without compromising on quality or credibility. For coaches, consultants, and creators, this means less time building infrastructure and more time focusing on clients and growth. 👉 Try Coaching Website Template Now: https://lnkd.in/d5Y_WZ4p 🔗 Read the full announcement: https://lnkd.in/dUxpY9fDAppWizzy Launches Coaching Website Template and One-Click Custom DomainsAppWizzy Launches Coaching Website Template and One-Click Custom Domains
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Kevin McKeand liked thisKevin McKeand liked this🚀 Startups don’t just need faster coding, they need faster product delivery. We compared Cursor and Flatlogic Generator from a business perspective: 💻 Cursor → accelerates developer productivity inside the IDE ⚙️ Flatlogic Generator → generates full-stack business apps with backend, database, APIs, auth, and deployment structure included The key difference is speed to production, not just speed to code. For founders and product teams, the winning AI tool is the one that reduces development time and technical overhead at scale. Read the full comparison: https://lnkd.in/dmxnq8zd #Startups #AI #SaaS #ProductDevelopment #WebDevelopment #VibeCoding #CursorAI #Automation #Founder #TechInnovationCursor vs Flatlogic Generator: Best Tool for Startups & SMBs in 2026Cursor vs Flatlogic Generator: Best Tool for Startups & SMBs in 2026
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Kevin McKeand liked thisKevin McKeand liked thisParking has always produced income. The question is whether asset owners are capturing what their parking assets should be producing. In his latest piece, Flash CBO Peter J Weiss explains that parking is the last system in commercial real estate operating outside the visibility, standards, and benchmarking that owners apply to every other line on the P&L. The shift he's calling for: from parking management to parking performance management — turning fragmented data, demand, and operations into measurable NOI advantage at the portfolio level. Read the article → https://lnkd.in/eSag58B5Parking is still managed like an operation. It should be managed like income. - Flash ParkingParking is still managed like an operation. It should be managed like income. - Flash Parking
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Kevin McKeand liked thisKevin McKeand liked thisThe renowned Philadelphia Museum of Art has modernized the parking experience across its 442-space garage and two surface lots. With Express Pay and Vision™, PMA has elevated the first and last impression for every guest—seamless arrivals and departures that match their world-class destination. Proud to support exceptional experiences from entry to exit. #MobilityInfrastructure #ParkingAutomation #ParkingInnovation #GuestExperience
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Kevin McKeand liked thisKevin McKeand liked thisOver the past year, we noticed something at Flatlogic: without even realizing it, we've been doing a lot of AI projects and integrations for various clients. We built AI systems for things like visual inspections, weather predictions, analyzing transcripts, pulling data from documents, automating CRM and ERP systems, creating operational dashboards and, of course, building AI chatbots :) A few weeks ago I decided to pause and realized: "Wait, this isn't just occasional AI work - this has become a key part of what we do constantly and repetitively for majority of our clients". So today we're officially launching our dedicated AI Consulting Services: [Link in the first comment!] The approach is simple: Find real business problems, messy processes, and repetitive tasks. Figure out where AI can really help-not just buzzwords. Quickly create useful AI pilots that deliver immediate benefits. Please let me know what you think!
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Kevin McKeand liked thisKevin McKeand liked thisTrijectory Holdings is actively syndicating our latest multifamily acquisition — and I wanted to share it with my network. We recently contracted on Cobblestone at Kali Lane a 24-unit, new-construction duplex community in Greenville, NC. All 24 units leased. Day-one cash flow. No lease-up risk. What drew us to this market: ECU's main campus (26,000+ students) and Brody School of Medicine create persistent rental demand Greenville is chronically undersupplied with quality, modern housing stock the Medical Center anchors a stable professional renter base year-round The asset itself: 12 duplex buildings, 3BR/2.5BA (2x 2BR), ~3,800 SF per building, attached garages, modern finishes that were built for long-term holds, not a quick flip. We structured this as a Reg D private placement for accredited investors who want passive exposure to cash-flowing residential real estate without the headaches of direct ownership. If you've been looking for a way to put capital to work in real estate or you're just curious how syndications work I'd love to connect. Full one-pager attached. DM me with any questions. — Vivek Shah | Managing Partner, Trijectory Holdings Josh Babitz Sam Metzler Trijectory Holdings #realestate
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Kevin McKeand liked thisKevin McKeand liked thisTwo years ago I was $600k in debt, again, and pacing the floors of our house in Mexico wondering if I'd made the biggest mistake of my life...again! Today I'm announcing our third location — and in July, my family and I are moving back to Carson City to help build it. Fox & Fire Pizzeria & Taproom is coming to Carson City, Nevada on August 1st. NY-style pizza. Our own Fox-brewed craft beer on tap. A hybrid QSR/fast casual model built for how people actually want to eat and drink in 2026. We bought a failing pizza shop for $80k. $20k down. Owner financing. It was doing $350k a year. We're going to more than double that. This isn't a vanity move. It's the next piece of a deliberate hub and spoke model we've been quietly building — where our two licensed breweries in Reno and Carson City supply craft beer directly to every location. No distributor. Full margin. Our beer, our brand, our economics. The Fox Restaurant & Brewery in Reno is on pace for $1.5M this year. Up 75% YoY. After back to back losing years. Fox & Fire is location three. There will be more. If you're in hospitality, small business, or just like watching something get built in real time — follow along. I'm going to start sharing exactly how we're doing it. #restaurantindustry #hospitalitylife #smallbusiness #nevada #carsoncity #craftbeer #restaurantgrowth #entrepreneurship
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Kevin McKeand liked thisKevin McKeand liked thisA special night with the Astronomic Founder Dinners community in Austin. This week, we brought together founders across four curated groups: 🚀 SaaS & Tech 💼 Agency & Consulting 🌸 Women 🌍 Open Group Each table had its own dynamic, but what stood out across all of them was the same thing: thoughtful founders, real conversation, generous insight, and the kind of connection that only happens when the room feels right. That is why we do this. No panels. No pitching. No forced networking. Just dinner with people who are actively building, figuring things out, and willing to share honestly. Thank you to everyone who joined us and made the evening what it was. We are excited to keep building a community where founders can meet in a way that feels personal, useful, and actually enjoyable. 🤍 If you’d like to join a future Founder Dinner, you can start here: 📝 Membership Form: https://lnkd.in/guS_eMEq 💬 Slack Community: https://lnkd.in/g5-bWFbC And if there is a founder in your circle who should be in the room next time, send them our way. We would love to meet them. #Astronomic #FounderDinners #AustinFounders #FounderCommunity
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Unreasonable Founder, No Plan B Interview Series
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💡 Did you know that curiosity is a superpower for entrepreneurs?
In my new podcast series, we’ll explore how staying curious and humble can lead to groundbreaking innovation.
Are you ready to embrace a "No Plan B" attitude? Let’s discuss!
#Curiosity #Innovation #NoPlanB #Entrepreneurship #Founders #MindsetMatters #Inspiration
Organizations
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Electronic Transactions Association
Chairman of Mobile Payments Committee
-The Mobile Payments Committee’s mission is to facilitate the global flow of e-commerce, while ensuring that the lives of every consumer touched are enriched and improved. The committee’s stated objectives are: - Enhance business relationships and network interoperability among merchants, card brands, networks, equipment manufacturers, and financial institutions. - Create proactive discussion on policy issues around data, privacy, security, billing, and fraud protection with state and federal…
The Mobile Payments Committee’s mission is to facilitate the global flow of e-commerce, while ensuring that the lives of every consumer touched are enriched and improved. The committee’s stated objectives are: - Enhance business relationships and network interoperability among merchants, card brands, networks, equipment manufacturers, and financial institutions. - Create proactive discussion on policy issues around data, privacy, security, billing, and fraud protection with state and federal legislators and regulators, including the FTC, CFPB, FCC, FED, FDIC, Commerce Department, etc. - Consumer and merchant education on mobile payments.
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Cellular Telecommunications Industry Association (CTIA)
Chairman of the Roaming Committee, Chairman of the Fraud Sub-Committee
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Nobody Studios
Startups don't just survive; they thrive when they embrace the struggle. 💪 Culture built on trust, speed, and shared resilience allows teams to move as one, even when faced with pivots and failures. Discover how an intentional culture prepares your startup for anything. Watch the full episode to learn more: https://lnkd.in/e9iwgC_r #StartupLife #BusinessGrowth #Innovation #CultureByDesign #NobodyStudios Barry O'Reilly
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Cojoy RevGen
Is your B2B SaaS company ready for hypergrowth, but your GTM engine is leaking capital? 🚀 The cost of a fragmented GTM strategy is measured in lost runway and reduced valuation. Before committing to a multi-hundred-thousand-dollar executive hire, de-risk your next growth phase with a high-efficiency diagnostic. Introducing the 2-Week GTM Audit & Strategy Roadmap. This intensive engagement is the fastest way to stop revenue leaks and build a predictable engine. It is not just a report—it's a concrete, board-ready 90-day plan that provides executive-level strategic direction and immediate pipeline guidance. Results are the only metric that matters: - 6x Pipeline Scale: Proven track record of accelerating global pipeline growth. - 86% CAC Reduction: Architected tech stack unification and ABM frameworks to drive immediate capital efficiency. Secure your strategy now and unlock immediate capital efficiency. Stop guessing and start growing. ➡️ Learn more about the 2-Week Blueprint and get the Strategy Roadmap: https://lnkd.in/eEFmgfsx
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Eastward Capital
One of the most powerful effects of venture debt is runway extension. When structured thoughtfully, debt can: ✔️ Add 6–12+ months of operating visibility ✔️ Strengthen negotiation leverage for the next raise ✔️ Provide capital for milestone acceleration Runway isn’t just time — it’s strategic flexibility. #VentureDebt101 #FounderTools #StartupFinance #EastwardInsights
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5th Line
Early-stage startups: Without strong financial resources and planning, your growth may stall. Key priorities at this stage include: 📈 Setting clear goals even if revenue is zero 📊 Building a flexible 12-month budget to track burn rate 🤝 Leveraging free resources like SBA and SCORE mentors Lay the groundwork for scalable growth with 5th Line—discover more: https://hubs.ly/Q03z33rR0 #earlystage #financialresources #startupgrowth
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Gary Graves
Excited to welcome Lance Scott, Russ Beckenstein, Shelli Clark, and Jessica R. to DealerCX. We’re building this company with operators who know the industry, understand the dealer, and care deeply about helping dealerships create better customer experiences across sales and service. #DealerCX #Automotive #DealershipLife #CustomerExperience #AutoIndustry #DealerOps #FixedOps #AutoRetail #TeamBuilding #StartupLife #CX
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Dan Debnam
Canada 🇨🇦 I’m heading your way In June, I’ll be at DSA Canada Connect 2026 and I want to talk about something I’m seeing across almost every Direct Selling company right now: the massive AI acceleration gap opening up. On one side: companies moving fast, solving real problems, building capability. On the other: companies stuck in planning mode, waiting for the “right” strategy. The difference isn’t technology. It’s action. In my session, I’m going to run you through something we’ve done with many of the 20+ direct selling companies we work with, something that accelerated their progress significantly. You’ll learn: → Where you are right now (honestly) → Where your immediate opportunities are → How to lead this, regardless of your title or technical background → Real examples of what’s working and what’s not And we’ll tackle both sides of this transformation: the incredible capability AI unlocks AND the very real risk it poses to human connection at the absolute heart of direct selling. It’s my first time in Canada (getting in a week early to explore), and I can’t wait to help you get on the right side of the acceleration gap. Thanks to Peter Maddox for inviting me and Ben Robinson for recommending me. If you’re there, see you in June!
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Triple S Ventures
🚀 VC Tip: Show traction, not just ambition Investors want to see evidence of execution. Ideas are cheap; results matter. ▪️Metrics matter more than words. Show engagement, growth, retention, or early revenue. ▪️Small wins count. Early customer feedback, pilot programs, or partnerships demonstrate credibility. ▪️Be transparent about challenges; a thoughtful founder anticipates problems and has a plan. Remember: traction doesn’t mean perfection, it means progress. Show us you can move fast, learn fast, and adapt faster. #VC #StartupTips #EarlyStageVC #FounderAdvice #TripleSVentures #StartupGrowth
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Force Management
The Power of Force Management. The Precision of AI. Meet Xcelerator™, powered by WINN.AI technology. By guiding and measuring adoption of revenue-driving behaviors in real time at the point of sale, Xcelerator allows sales organizations to automate consistent high-level execution. See how Xcelerator improves pipeline visibility, guides effective customized coaching and enables customer interactions that increase win rates and deal sizes across the board: https://bit.ly/4ivaF2t Welcome to the new era of sales performance.
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Bradley Geldenhuys
One of the clearest examples I’ve seen of how vendor oversight can evolve comes from our work with PKF Littlejohn. They wanted a way to avoid sending the same questionnaire to every supplier and wasting time on irrelevant back and forth. That request became the foundation of Vendifi’s automated, risk-based questionnaires. By mapping each vendor to the business process, data and department they interact with, the system identifies what’s truly critical. Vendors only receive the questions and evidence requests that apply to them. Nothing more, nothing less. The result is faster onboarding, cleaner due diligence and a process that finally reflects the reality of modern supply chains – focused, proportionate and easy to manage.
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