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Connor McLeod
Venture Capital & Startup Funding Strategy for Founders5.6K followers

Connor McLeod

Building an AI-native holdco at SageCreek AI | We acquire service businesses and own the EBITDA / Rev expansion | YC W19 | Ex-JPMorgan AI

72 posts analyzed1.5K total likes414 comments37 repostsView on LinkedIn
TL;DR - what makes Connor's LinkedIn work

Connor McLeod writes tactical founder advice in the VC/startup space, posting 5.5x per week with medium-length posts (80-180 words) that average 27 engagements. His most distinctive move is leading with contrarian claims that flip conventional wisdom (e.g., 'You need customers before you need a platform'), then backing them with specific experience and pattern recognition from 'hundreds of companies.'

Cadence

5.5/wk

72 posts in 30d

Avg engagement

27

avg per post

Conversation

21.6%

comments / total

Repost rate

1.9%

reposts / total

Top format

story

Best window

Wed Β· 12 PM CET

Voice & tone

Connor writes like a battle-tested operator who's seen what works and what doesn't. He's direct without being harsh, mixing casual confidence ('I get it') with earned credibility ('I've watched hundreds of companies burn through runway'). He uses short, punchy sentences to create momentum and sprinkles in self-aware humor ('maybe I'll post about this some other time... πŸ‡'). The tone says: I've been in the trenches, I'm not selling you theory, and I'm willing to say what everyone's thinking but won't say out loud.

Signature phrases

  • β€œI've watched hundreds of companies”
  • β€œHere's the thing:”
  • β€œThat's not reckless. That's risk mitigation.”
  • β€œThe companies that succeeded? They sold first, then scrambled to build.”
  • β€œI've seen and experienced in the 0-to-1 trenches”
  • β€œTrust me. I've looked.”

Top 3 posts, dissected

Their highest-engagement posts, broken down line by line. Steal the structure.

#1Top post breakdown
96343
The post242 words

You need customers before you need a platform. I get it. Your engineering team wants to build it "right" from day one. Potential investors are asking about scalability. Your friends and advisors are warning about technical debt. Here's the thing: Most startups die with perfectly architected products that no one wanted. I've watched hundreds of companies burn through runway building enterprise-grade platforms before validating a single customer would pay. They had Kubernetes clusters handling zero traffic. They had 99.9% uptime for services no one used. The companies that succeeded? They sold first, then scrambled to build. That's not reckless. That's risk mitigation. Your first 10 customers aren't buying your infrastructure. They're buying your ability to solve their specific problem. They know you're early. They expect rough edges. What they need is confidence you understand their pain deeply enough to eventually eliminate it. The vibe-coded MVP isn't about cutting corners. It's about being surgical with your focus. Design the experience. Sell the vision. Build what customers actually pay for. I've seen and experienced in the 0-to-1 trenches with dozens of founders who built real businesses this way. They didn't start with microservices. They started with customer conversations and Stripe payment links. The result? Product-market fit in months, not years. Revenue before Series A. Technical debt that's actually worth paying down because customers exist to demand it. Stop building solutions to imaginary problems. Start solving real problems with imaginary products. Then make them real.

Hook

The hook 'You need customers before you need a platform' is a direct contradiction of what engineering teams and investors typically push for. It stops the scroll because it's immediately actionable and challenges the reader's current approach. The specificity (customers vs. platform, not just 'build lean') makes it memorable.

Structure

Opens with the contrarian claim, then acknowledges the counter-pressure (engineering team, investors, advisors), then pivots to pattern evidence ('Most startups die with perfectly architected products'), then provides concrete examples (Kubernetes clusters, 99.9% uptime), then reframes the solution (sell first, build second), and closes with a reframing of MVP as 'surgical focus' not 'cutting corners.'

Stylistic moves
  • Acknowledge the objection first - 'I get it. Your engineering team wants to build it right from day one.' This disarms resistance.
  • Use vivid failure imagery - 'Kubernetes clusters handling zero traffic' and '99.9% uptime for services no one used' make the problem tangible.
  • Reframe the narrative - 'That's not reckless. That's risk mitigation.' Flips the moral judgment.
  • Contrast the two paths - 'The companies that succeeded? They sold first, then scrambled to build.' Short, punchy, memorable.
Close / CTA

Ends with 'I've seen and experienced in the 0-to-1 trenches with dozens of founders who bu...' (truncated). The CTA is implicit: apply this logic to your startup. The post drives comments because it challenges a deeply held belief and offers a counterintuitive path forward that readers want to debate or validate.

Steal this

Lead with the contrarian claim, immediately acknowledge why readers believe the opposite, then provide pattern evidence and vivid examples to make the new claim feel earned and safe to adopt.

#2Top post breakdown
104270
The post301 words

Last week an incredible chapter of my life closed. After a lot of thought, discussion and reflection, my ride at Nerd, and Perspect, has come to an end. I learned and accomplished a lot - from scaling the product and design team from 1 to ~25, shipping a blockchain loyalty plat…

Hook

The hook 'Last week an incredible chapter of my life closed' is emotionally loaded and vague enough to create curiosity. It signals a major life event without revealing it, forcing readers to keep reading. The phrase 'incredible chapter' is positive, so readers expect a win or learning, not a failure.

Structure

Opens with the emotional hook, then reveals the transition (leaving Nerd/Perspect), then provides a detailed recap of accomplishments (scaling team 1 to 25, shipping blockchain loyalty platform, growing MRR from thousands to $100k+), then signals openness to new opportunities (advisory, coaching, startup groups), and closes with gratitude and a call to action for community.

Stylistic moves
  • Quantify the wins - '1 to ~25,' 'few thousand dollars of MRR to more than $100k MRR,' '0 to a few hundred DAUs in a few months.' Numbers make the story credible.
  • Praise the team - 'deeply motivated by our mission, highly skilled, focused on creating real value.' This positions Connor as a leader who recognizes talent, not just a solo achiever.
  • Signal openness without desperation - 'I'm always open to discussing interesting opportunities, startups, advisory, and coaching!' Leaves the door open without begging.
  • End with community - 'Let me know if you or anyone you know has a startup founder group I could join.' Invites readers to help, making them feel useful.
Close / CTA

Closes with 'Here's to all the Nerds and all the awesome friends I had the chance to innovate with along the way.' This is a gratitude play that drives comments because readers want to either congratulate him, ask about the next move, or offer opportunities. The post is a soft landing announcement that builds goodwill.

Steal this

When announcing a transition, lead with emotion, back it with quantified wins, praise your team generously, and end with openness to community. This drives engagement because readers feel invited to participate in your next chapter.

#3Top post breakdown
83171
The post15 words

I’m happy to share that I’m starting a new position as Pirate at Obruni Labs!

Hook

The hook 'How many of your developers are playing League of Legends when they should be working? 🚨' is provocative and assumes a problem (low productivity). The emoji signals urgency and prevents the question from feeling accusatory. It's designed to make engineering leaders and managers feel seen and slightly defensive, which drives engagement.

Structure

Opens with the provocative question, then cites the source (Dimitar Bakardzhiev on Andrew Boyagi's thread), then presents two competing assumptions (business leaders think % of non-workers is high; engineers think it's low), then flips the equation (Netflix/productivity correlation is wrong; strategy/culture is the real driver), then provides a solution framework (outcome-driven companies, good strategy, clear timelines, visionary leaders).

Stylistic moves
  • Use emojis as visual shorthand - 'πŸ™…β€β™‚οΈ' for dismissal, 'πŸ“ˆ' and 'πŸ“‰' for correlation, 'πŸ’©' for bad outcomes. This makes the post scannable and adds personality.
  • Create a false equation, then flip it - 'Netflix watching->πŸ“ˆ = Productivity->πŸ“‰' vs. 'Strategy/Culture->πŸ’© = Outcomes of Eng Teams->πŸ’©.' This is a pattern interrupt that forces re-reading.
  • Acknowledge the rabbit hole - 'maybe I'll post about this some other time... πŸ‡' This is self-aware and invites future engagement.
  • Provide a solution framework - The bullet points at the end give readers actionable steps, which increases perceived value.
Close / CTA

The post is truncated, but the structure suggests it ends with a framework for leaders to implement. The high comment count (32 out of 83 engagement) suggests readers are debating the premise, which means the hook successfully triggered disagreement and discussion.

Steal this

Use a provocative question to surface a hidden assumption, then flip the conventional wisdom with a better equation or framework. This drives comments because readers want to either defend the old model or celebrate the new one.

What drives their engagement

Drives comments

Connor's posts drive comments (21.6% conversation index) by presenting contrarian claims that challenge readers' current beliefs or practices. Posts like 'You need customers before you need a platform' and 'How many of your developers are playing League of Legends' invite debate because they flip conventional wisdom and ask readers to reconsider their approach.

Drives reposts

Repost rate is low (1.9%), suggesting Connor's content is more personal advice than universal wisdom. Reposts likely come from posts with clear frameworks or actionable solutions (e.g., the engineering culture post with bullet-point solutions) that readers want to share with their teams.

Savability

Low savability signal. Connor optimizes for reach and comment-driven discussion, not reference material. His posts are meant to spark immediate debate and reflection, not serve as long-term resources.

Content pillars

Product-Market Fit & MVP Strategy

35%

Teaches founders to validate customer demand before over-engineering, using pattern recognition from failed startups to argue for speed over perfection.

Engineering Culture & Team Dynamics

25%

Explores how strategy, leadership clarity, and outcome-driven thinking affect engineering productivity and team morale.

Personal Career Milestones & Transparency

20%

Shares wins, transitions, and lessons learned from scaling teams and products, positioning himself as a relatable founder-operator.

Community & Events

15%

Announces founder meetups, hackathons, and networking opportunities, using scarcity and social proof to drive attendance.

AI & Emerging Tech Applications

5%

Covers practical AI tooling and data science use cases for startups, tied to his current work and interests.

Hook patterns

Contrarian Flip

Restate the conventional wisdom, then immediately flip it with 'Here's the thing:' or 'That's not X, that's Y.'

β€œYou need customers before you need a platform. / Here's the thing: Most startups die with perfectly architected products that no one wanted.”

β†’ Creates cognitive dissonance that forces readers to keep reading to resolve the tension.

Provocative Question

Ask a question that implies a problem or assumption, often with an emoji to signal urgency or humor.

β€œHow many of your developers are playing League of Legends when they should be working? πŸš¨β€

β†’ Questions activate reader participation and make them feel seen; the emoji signals tone and prevents misinterpretation.

Scarcity + Authority

'You can't find [X] anywhere. Trust me. I've looked.' Establishes both rarity and credibility in one move.

β€œYou can't find events like this anywhere. Trust me. I've looked.”

β†’ Combines FOMO with earned credibility, making the reader believe the claim is backed by real search effort.

Personal Milestone Reveal

Open with a life event ('Last week an incredible chapter closed') that signals a story worth reading.

β€œLast week an incredible chapter of my life closed.”

β†’ Taps into curiosity and positions the founder as human and transparent, building parasocial connection.

Specific Metric + Outcome

Lead with a concrete number or achievement tied to a company or role, then expand on the learning.

β€œI'm happy to share that I'm starting a new position as Pirate at Obruni Labs!”

β†’ Gives readers a concrete reason to engage and signals the post will contain insider knowledge.

Top-performing hooks

1

β€œYou need customers before you need a platform.”

133 engagements96 likes Β· 34 comments Β· 3 reposts
2

β€œLast week an incredible chapter of my life closed.”

131 engagements104 likes Β· 27 comments
3

β€œI’m happy to share that I’m starting a new position as Pirate at Obruni Labs!”

101 engagements83 likes Β· 17 comments Β· 1 reposts
4

β€œHow many of your developers are playing League of Legends when they should be working? πŸš¨β€

83 engagements50 likes Β· 32 comments Β· 1 repostsProvocative Question

β†’ The post challenges a common business leader assumption with a provocative opening question, then reframes the real problem from employee laziness to poor strategy/culture, making it highly relatable

5

β€œYou can’t find events like this anywhere.”

76 engagements59 likes Β· 10 comments Β· 7 repostsContrarian Claim

β†’ The post combines exclusivity messaging ('can't find events like this anywhere') with specific, tangible incentives (cash prizes, networking with 50+ experts) and a clear problem-solution narrative th

6

β€œLinkedin - I have to tell you something I'm absolutely STOKED about.”

73 engagements55 likes Β· 11 comments Β· 7 reposts
7

β€œI had lunch yesterday with a Utah founder that sold his startup to Bill Gates.”

72 engagements58 likes Β· 14 comments
8

β€œI'm 90% sure Greg Butterfield set up OpenClaw on his laptop last week because he suddenly started responding to emails at 3am with perfect grammar.”

52 engagements30 likes Β· 22 comments
9

β€œTalked to a marketing VP this week that said he gets 10 AI pitches a week.”

49 engagements37 likes Β· 12 comments
10

β€œMeasuring outputs alone is weak sauce. Productivity MUST be tied to outcomes.”

47 engagements31 likes Β· 14 comments Β· 2 repostsBold Statement

β†’ The post establishes authority by respectfully challenging a recognized expert (Abi Noda) while providing a nuanced counterargument backed by multiple thought leaders, creating engagement through inte

What works

  • Contrarian claims with pattern evidence - Top post #1 (133 eng) opens with 'You need customers before you need a platform' and backs it with 'I've watched hundreds of companies burn through runway.' The specificity of 'hundreds' makes the claim feel earned, not just opinion.
  • Emotional transparency in career announcements - Post #2 (131 eng) uses 'Last week an incredible chapter of my life closed' to create curiosity, then quantifies wins (1 to 25 team members, thousands to $100k+ MRR). This mix of emotion and metrics drives engagement because readers feel invited into a real journey.
  • Provocative questions with emoji signaling - Post #4 (83 eng) uses 'How many of your developers are playing League of Legends when they should be working? 🚨' to surface a hidden assumption. The emoji prevents the question from feeling accusatory and signals tone.
  • Scarcity + authority combo - Post #5 (76 eng) opens with 'You can't find events like this anywhere. Trust me. I've looked.' This two-step move (scarcity + credibility) makes the claim feel both rare and verified.
  • Equation flips - Post #4 uses 'Netflix watching->πŸ“ˆ = Productivity->πŸ“‰' then flips to 'Strategy/Culture->πŸ’© = Outcomes of Eng Teams->πŸ’©.' This visual pattern interrupt forces re-reading and makes the insight stick.
  • Specific metrics in personal updates - Post #2 includes '1 to ~25,' 'few thousand dollars of MRR to more than $100k MRR,' and '0 to a few hundred DAUs in a few months.' These numbers make the story credible and give readers concrete benchmarks to compare against their own work.

Steal this for your own LinkedIn

  • Start your next post with a contrarian claim that flips what your audience believes, then immediately acknowledge why they believe the old way. Use 'Here's the thing:' or 'That's not X, that's Y.' to signal the flip.
  • When sharing a win or transition, lead with emotion ('Last week an incredible chapter closed'), then quantify the impact (numbers, metrics, team size). This mix of heart and proof drives both comments and credibility.
  • Use provocative questions with emojis to surface hidden assumptions your audience holds. The question should make readers slightly defensive or curious, not accusatory. The emoji prevents misinterpretation.
  • Back every claim with pattern evidence from your experience. Use phrases like 'I've watched hundreds of companies' or 'I've seen and experienced in the 0-to-1 trenches' to signal that your advice is earned, not theoretical.
  • Post on Wednesdays at 11 UTC if your audience is US-based founders and operators. Aim for 150-250 words to balance depth with scannability. Longer posts (180-350 words) average 2.5x more engagement than short posts.
  • End career announcements or major updates with openness to community ('Let me know if you or anyone you know has a startup founder group I could join'). This invites readers to participate in your next chapter and drives comments.

Compare Connor with…

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Posting patterns

Rhythm

Connor posts 5.5 times per week (72 posts in 72 days), maintaining consistent presence with no gaps. This high frequency keeps him visible in followers' feeds and signals active engagement with the community.

Best window

Posts perform best on Wednesdays at 11 UTC. This timing likely captures US business hours (early morning on the East Coast, mid-morning on the West Coast) when founders and operators are checking LinkedIn during work.

Length sweet spot

Medium-length posts (80-180 words) are his bread and butter at 47% of posts and averaging 21 engagement. However, long-form posts (180-350 words) average 53 engagement, suggesting that when he goes deeper, readers reward it with more interaction. The sweet spot is 150-250 words: long enough to provide pattern evidence and examples, short enough to hold attention.

Engagement by day

Wed
27

Content mix

story4% Β· 3 posts

avg 22 engagements per post

Connor's format mix works because he balances tactical advice (product strategy, engineering culture) with personal transparency (career moves, team wins). The high posting frequency (5.5x per week) keeps him visible without overwhelming followers, while the medium-length sweet spot (80-180 words) allows him to provide pattern evidence and examples without losing attention. His low story rate (4%) suggests he reserves narrative for major announcements, which makes those posts feel more significant when they arrive.

Post length distribution

medium (80-180)47% Β· avg 21
short (30-80)21% Β· avg 19
long (180-350)18% Β· avg 53
micro (<30 words)11% Β· avg 19
very long (350+)3% Β· avg 29

Hook style mix

contrarian claim3Γ— Β· avg 36
bold statement9Γ— Β· avg 24