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Jason Bennett

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You're a visionary technical founder with a brilliant idea, but face some or all of these challenges: ↓. Struggling to nail your product/market fit and business model ↓. Stalled growth and rapidly burning through your runway ↓. Lacking the processes and team to scale from seed to Series A ↓. Unsure how to craft a compelling pitch and impress investors ↳ Founder overwhelm - trying to do it all yourself All while months or years go by and competitors are scaling up. I've been in your shoes. I'm a 3x technical founder who's: → Exited 2x as a founder/principle in B2B software companies; → Has raised $MM in capital and understands the game; → Mentored founders like you to launch, raise, and scale. I combine decades of operator experience with a scaleup mindset Working with me, you'll gain a trusted mentor to help you: ↗︎ Fine-tune your business model and uncover predictable, scalable growth ↗︎ Implement scalable processes and align teams to go from seed to A-round ↗︎ Craft a winning pitch deck and nail your narrative ↗︎ Become a magnet for top-tier investors and A-Player talent ↗︎ Transform from founder to CEO with more time to do what you love An experienced guide is no longer optional. With the right playbook and partner, you can beat the odds, attract capital, talent, and thrive in business, and life. Let me help you go from seed to scale to exit. Reach out today!

Check out Jason Bennett's verified LinkedIn stats (last 30 days)

Followers
9,078
Posts
5
Engagements
43
Likes
35

What is Jason talking about?

startup
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  • engagement

Who is engaging with Jason

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Dr. Hajra Kirmani Cloud Architect(Azure/AWS/Artificial Intelligence) profile picture
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Jason Bennett's Best Posts (last 30 days)

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𝗬𝗼𝘂 𝘀𝗮𝘆 𝘆𝗼𝘂 𝘄𝗮𝗻𝘁 𝗴𝗿𝗼𝘄𝘁𝗵… 𝗯𝘂𝘁 𝘆𝗼𝘂 𝗸𝗲𝗲𝗽 𝗱𝗼𝗶𝗻𝗴 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 𝘀𝗵𝗶𝘁. Most founders aren’t stuck because of ability, the market, or whatever. They’re stuck because of their mindset. I’ve been there and modeled this post around my experiences and what I see coaching technical CEOs. Let’s paint a picture: You hired advisors → an agency → bought the courses  → maybe even hired a coach. But nothing’s really changed. → Revenue’s still flat. → You’re still chasing shiny objects. → You’re still “too busy” to fix what’s broken. Sound familiar? 🥊 Truth: You didn’t hire help. You hired insurance. Insurance to keep telling you you’re on the right track. Insurance to feel like you’re “doing something.” And, what you really did, was try to outsource growth without putting in the work first; and Didn’t change anything to think and do different as a leader. 🥊 🥊 Harder truth: You want to scale, but you won’t commit. You want clarity, but you resist decisions. You want freedom, but you keep building your own prison. Founders who win do three things differently: (1) They kill their darlings. ↳ The thing you’re most attached to? It’s probably what’s keeping you stuck. You don’t need another feature; or another round of polishing your brand. You need to sell it → Scale it → Focus… (2) They stay uncomfortable. ↳ If it doesn’t scare you a little, you’re not playing a big enough game. No one becomes a CEO by sticking to what they know. They put themselves in situations that stretch them  →  make bold decisions faster → listen to people who challenge them. (3) They learn faster than they fail. ↳ Growth isn’t a win/loss game. It’s a data game. You’re going to screw things up. That’s not the problem. The problem is wasting 6 months pretending what you’re doing is “working.” Data doesn’t lie.  You’re either making progress — or rationalizing stagnation. Get real with yourself, make a plan, and commit. 💡 So what’s your next move? --------------------------------------- You built the product. I help build the business your product deserves. 📌 Think you’re the exception? Let’s talk. DM me or book a call.


10

𝗚𝗮𝗺𝗲-𝗖𝗵𝗮𝗻𝗴𝗶𝗻𝗴 𝗥𝗲𝗳𝗿𝗮𝗺𝗲: 𝗪𝗵𝗼 𝗱𝗼 𝘆𝗼𝘂 𝗻𝗼𝘁 𝘀𝗲𝗿𝘃𝗲? Clarity isn’t just about your ICP—it’s also who you’re willing to walk away from. Your perfect customer isn’t just a nice-to-have… they’re your 𝘰𝘯𝘭𝘺 shot at leverage. Get this wrong and you’ll: ↓  waste time,  ↓  confuse your team,  ↓  write garbage content, and  ↓  sell the wrong thing to the wrong people. Worse? You’ll 𝘣𝘶𝘪𝘭𝘥 𝘵𝘩𝘦 𝘸𝘳𝘰𝘯𝘨 𝘱𝘳𝘰𝘥𝘶𝘤𝘵. Here’s the hard truth: if you're getting ghosted, rescheduled, or ignored — it’s probably because your messaging is landing with people who shouldn’t have been on your radar in the first place. Here’s an idea: 👉 Define your dartboard: ↗︎  Who is an absolute 𝘯𝘰? ↗︎  What disqualifies a prospect immediately? ↗︎. What patterns have you seen in customers that ghost, waste your time, or churn? Use this to build your "Hell No" list. 🥊 It’s as powerful as your perfect customer ICP. What’s your next move? ---------------------------------------- I help build the business your product deserves. If you’re having trouble dialing in your perfect customer profile, Let’s Talk.  📌


7

𝗕𝗲 𝘁𝗵𝗲 𝗼𝗯𝘃𝗶𝗼𝘂𝘀 𝗰𝗵𝗼𝗶𝗰𝗲 𝗼𝗿, 𝗯𝗲 𝗶𝗻𝘃𝗶𝘀𝗶𝗯𝗹𝗲 The market is louder, faster, and competition is more fierce than ever. You’re not just fighting for attention… You’re fighting for relevance. And, the brutal truth? 𝗚𝗲𝗻𝗲𝗿𝗶𝗰 = 𝗶𝗻𝘃𝗶𝘀𝗶𝗯𝗹𝗲. 🥊 You can’t just say “better UX” or “built with AI” anymore. That’s wallpaper. Everyone’s claiming it. 𝗬𝗼𝘂 𝗻𝗲𝗲𝗱 𝗮 𝘂𝗻𝗶𝗾𝘂𝗲 𝗲𝗱𝗴𝗲. 𝗔 𝗺𝗼𝗮𝘁. 𝗔𝗻 𝘂𝗻𝗳𝗮𝗶𝗿 𝗮𝗱𝘃𝗮𝗻𝘁𝗮𝗴𝗲. Start by asking yourself: ↳ 𝗜𝘀 𝗶𝘁 𝘁𝗶𝗺𝗶𝗻𝗴? (New regulation? Shift in buyer behavior?) ↳ 𝗜𝘀 𝗶𝘁 𝗮𝗰𝗰𝗲𝘀𝘀? (Proprietary data? Deep networks?) ↳ 𝗜𝘀 𝗶𝘁 𝗲𝘅𝗽𝗲𝗿𝘁𝗶𝘀𝗲? (You’ve done this before. You’ve lived the customer’s pain.) ↳ 𝗜𝘀 𝗶𝘁 𝗶𝗻𝘀𝗶𝗴𝗵𝘁? (You see a problem others can’t even name yet.) 𝗪𝗵𝗮𝘁𝗲𝘃𝗲𝗿 𝗶𝘁 𝗶𝘀 — 𝗡𝗔𝗠𝗘 𝗜𝗧, 𝗖𝗟𝗔𝗜𝗠 𝗜𝗧, 𝗮𝗻𝗱 𝗕𝗨𝗜𝗟𝗗 𝗔𝗥𝗢𝗨𝗡𝗗 𝗜𝗧. If you can’t answer the question: "𝘞𝘩𝘺 𝘴𝘩𝘰𝘶𝘭𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘱𝘪𝘤𝘬 𝘶𝘴 𝘰𝘷𝘦𝘳 𝘢𝘯𝘺𝘰𝘯𝘦 𝘦𝘭𝘴𝘦?”… without stammering, you don’t have a real business advantage yet. The good news? Your edge doesn’t have to be massive today. It just has to be 𝘳𝘦𝘢𝘭. And you have to make it 𝘰𝘣𝘷𝘪𝘰𝘶𝘴. Examples: 💥 "We’re the only platform with compliance baked in by design, not as an add-on." 💥 "We help [ICP] go from X → Y in half the time of anyone else." 💥 "We’re the founders who scaled [similar company] and exited." That’s what makes buyers lean in. That’s what creates 𝘱𝘶𝘭𝘭 instead of 𝘱𝘶𝘴𝘩. 𝗢𝘄𝗻 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝗺𝗲𝗮𝗻𝗶𝗻𝗴𝗳𝘂𝗹 — 𝗼𝗿 𝗴𝗲𝘁 𝗹𝗼𝘀𝘁 𝗶𝗻 𝘁𝗵𝗲 𝗻𝗼𝗶𝘀𝗲. What’s your next move? ---------------------------------------- I help build the business your product deserves. If you’re having trouble dialing in your unique value, Let’s Talk.  📌


7

I had to chose and commit to the game before I could win You’re not just building a product or delivering a service, you’re building a business. Startups die when they chase everything and commit to nothing. So first, define your game. (?)  What are you really building (in your customer’s words)?  (?)  What does 𝘸𝘪𝘯𝘯𝘪𝘯𝘨 look like for you — 1 year, 3 years, 10 years from now?  (?)  Is your entire company aligned to that vision, or are you winging it? This is the strategy work most founders skip because it feels like “fluff.” But the companies that win? They make every decision based on the game they 𝘤𝘩𝘰𝘴𝘦 to play. 🔥 “We’re building a $10M ARR business that 3x’s efficiency for [target customer].” 🔥 “We’re on track to own 20% of a category no one’s thought to name yet.” 🔥 “For [target customer], we’re the only [category] that [differentiator].” These are clear. And clarity makes every future decision easier. What’s your next move? ---------------------------------------- I help build the business your product deserves. If you’re having trouble getting and staying on point, DM me or book a call.  📌


6

4 things I wish someone told me about building leverage It’s easy to confuse motion with progress. The Slack messages. The “quick calls.” The endless firefighting. But here’s the uncomfortable truth: 𝗬𝗼𝘂’𝗿𝗲 𝗻𝗼𝘁 𝘀𝗵𝗼𝗿𝘁 𝗼𝗻 𝘁𝗶𝗺𝗲. 𝗬𝗼𝘂’𝗿𝗲 𝘀𝗵𝗼𝗿𝘁 𝗼𝗻 𝗹𝗲𝘃𝗲𝗿𝗮𝗴𝗲. 🥊 If you want to actually grow (and not just survive), you need to be brutally honest: ↳ What are the 2–3 moves that would 10x the business if you focused hard on them? ↳ Where are you wasting cycles and chasing noise? ↳ What’s one initiative right now you could double down on — and be twice as far, twice as fast? The CEO’s real job isn’t to do more. It’s to identify and bet on the right few things. Period. Here’s a simple drill you should run weekly: (No excuses. No fluff.) 1/ Where are we wasting effort? ↳ Meetings that produce no decisions. Projects with no clear outcomes. 2/ What is compounding? ↳ Look hard. One channel, one partner, one customer segment is probably quietly working. Find it. 3/ Where are we stuck? ↳ If you don’t know your team's biggest blockers by Wednesday each week, you’re flying blind. 4/ What would unblock progress fastest? ↳ It’s usually simpler than you think: Clearer goals, tighter priorities, more ruthless focus. Leverage isn't a nice-to-have. It’s the difference between a business that compounds… And a business that collapses under its own weight. You don’t scale by doing everything. You scale by doing the right few things 10x harder. What’s your next move? --------------------------------------- I help build the business your product deserves. If you’re stuck in motion and not seeing real momentum, let’s talk. 📌


5

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