Grace Gong is the founder of Smart Venture Media and the host of two well-known VC podcasts: Smart Venture Podcast (SVPpro.com) and Venture with Grace, a daily show. She is an angel investor in the AI sector, a super angel & venture scout for Alumni Ventures, Advisor at Berkeley SkyDeck. 

Her podcasts have featured high-profile guests such as C-level executives and VPs from companies like Google, Meta, Amazon, Microsoft, Sephora, Dunkin' Donuts, Chipotle, Adidas, Pepsi, Instagram, Deloitte, Reddit, DoorDash, Pinterest, Cisco, Salesforce, NVIDIA, Snowflake and more. Additionally, she has interviewed Managing Partners from top funds, many of whom have appeared on the Forbes Midas List, as well as unicorn founders from companies like Craigslist, Square, Loom, and Glean. Grace regularly posts about technology, venture capital, and entrepreneurship and has been recognized as a LinkedIn Top Voice in Finance. She is also a #1 Bestselling author in the VC category on Amazon New Release. Before founding Smart Venture Media, she worked in venture capital and private equity. If you share her interests, feel free to connect with her on LinkedIn @GraceGong.


2025: Spoke at AWS, Seattle Startup Summit, event collab w/ various funds. Hosted Smart AI Leadership Summit and Smart AI 100 Summit SmartVentureMedia.com (10M+ impressions/ yr) Companies/ funds we have worked with including Microsoft, Snowflake, Sequoia, Vercel, Alumni Ventures, Amazon AWS, Auth0 among others.
2024: Venture with Grace daily live podcast (top 10%) features top GPs, LPs, execs, and founders. Angel investing in the AI space. 1.5M+ impressions in 7 days end of 2024.
2023: Spoke at LinkedIn HQ, ads clients: VC funds, startups, big tech.
2022: LinkedIn Top Voice in Finance, LinkedIn's creator accelerator fellow; clients including big tech & unicorn startups, speaking engagements: Dell, Microsoft
2021: CEO of Smart Venture Media (monetized, joined VC fellowship)
2020: Podcast - Smart Venture Podcast (top 1.5% among 3.4M podcasts globally, listeners in 100+ countries)
2019: PE 
2018: VC  
2017: Book 2 - How To Be A VC (No.1 new release on Amazon VC category; ft. 22 investors on the Forbes Midas List - investors who invested in Facebook, Twitter, LinkedIn, Apple, etc) 
2016: Book 1 - The Last Key To Success (ft. 21 founders on Forbes 30 under 30)
2014: Master's + PE
2013: UIUC

🤓 svppro.com
🚀 Stay connected: https://linktr.ee/gracegong115
💼 Book an ad on my podcast | Book me to speak at your conference/ events: 
grace@smartventurepod.com
💰Book to chat with me: https://intro.co/gracegong

Grace Gong

CEO CLUB is officially live! 

20 handpicked founders and VCs in the room: Founder who raised $100M at seed/Series A. VCs who backed the hottest companies in Silicon Valley like Higgsfield and Micro1. Big tech SVP. W26 Y Combinator companies we knew would be the ones to watch.

Mid-dinner, a founder pulls out his laptop—because the work doesn't stop.
That's CEO CLUB.

Michelin-trained chef. Private venue. One minute you're talking about Disneyland, the next you're solving a bug so your customer can process million-dollar transactions.

This isn't another founder dinner where people swap LinkedIn profiles and ghost each other by Tuesday.

It's a curated series connecting the sharpest founders with the VCs writing meaningful checks and the builders who need what you're making. Breakout sessions. Real intros. A community that actually picks up where dinner left off.
You weren't in the room. But next time? That could change.

↓ Apply below ↓

CEO CLUB by Venture with Grace.

None of this happens without our incredible partners Vanta and WilmerHale.
 
Thank you for believing in this vision and making CEO CLUB possible. 🙏

#CEOClub #VentureCapital #FounderDinners #SiliconValley

Just saw Guy Kawasaki in Hawaii.

The guy who made the Macintosh a religion before anyone called it “evangelism marketing.”

40+ years in tech and still going.
That’s the game. Longevity isn’t about one big win. It’s about showing up for decades.

2026 is going to be wild for Smart Venture.
Can’t announce what we’re building yet, but it’s the biggest thing we’ve ever done.

More soon. ☀️

#VentureCapital #Startups #AI #Marketing #Entrepreneurship

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My top takeaways from Denise Persson, CMO at Snowflake:

Sales and Marketing are “one brain in two bodies.” The classic friction between these departments is a growth killer. At Snowflake, they functioned as a single unit. Marketing doesn’t "hand off" to Sales; they co-pilot the entire revenue journey.

Kill the MQL; focus on Pipeline. Stop celebrating 20,000 leads if they don’t convert. Denise’s team measured success by qualified meetings with the specific accounts Sales actually wanted. Align your metrics with business outcomes, not department vanity.

Say “Yes” before you’re ready. Denise accepted a Global Head of Marketing role at 27 while feeling completely unqualified. Don’t wait for the "perfect" moment of readiness. If a leader you respect bets on you, bet on yourself and learn on the fly.

Positioning must be “Believable” for the stage. Snowflake didn't start by claiming to be a "Data Cloud"—no one would have believed a tiny startup. They started with "Data Warehouse built for the cloud." You earn the right to a massive category by winning a specific, high-pain wedge first.

Verticalize to win the Enterprise. To scale from millions to billions, you must stop "selling technology" and start "selling business outcomes." Speak the specific language of finance, healthcare, and retail. Generalists get ignored; specialists get hired.

AI is about “Hyper-Personalization at Scale.” AI won't replace great marketers, but it will replace the manual drudgery. The goal is a closed-loop process that serves the right message to the right person in real-time, without a human pulling every lever.

Preserve a “Truth-Telling” circle. Success creates an echo chamber. You need a board of advisors (or a partner) who will ground you and tell you the painful truth about your strategy. Feedback is a gift you have to earn through radical trust.

None of it matters—and that’s liberating. We’re on a blue marble drifting through space. Play the sport with everything you’ve got—be intense, be world-class—but never forget it’s just a sport. That perspective is the backstop that makes the intensity sustainable.

Full pod link in first comment. 

#VentureWithGrace #Snowflake #GTM #MarketingStrategy #TechLeadership #SaaS

10pm work call. Walking out of the airport. Rainbow waiting.

January 1st.

Everyone’s posting their crazy goals today. I’m thinking about something different.

You don’t need the perfect plan on day one.
You just need to walk through the rain.

The rainbow shows up when it shows up. Not before. Not because you manifested it or built the perfect strategy deck.

Because you kept walking.

2026 isn’t about the goals you set today. It’s about what you do when it’s 10pm and you’re tired and it’s raining and you still show up.

The rainbow shows up when you keep walking.

#Entrepreneurship #StartupLife #FounderJourney #VentureCapital #2026

Never thought I’d be so important that people are DMing me to “go back to work” 😂

I’m on vacation til Friday. But let’s be real - work doesn’t wait.

I work through every vacation. Last one? 10 days before our conference, grinding til 2 AM every night.

I don’t believe in work-life balance.
If you want to build something that matters, you have to go ALL IN.

But here’s what I DO believe in:
Building something so meaningful that “work” stops feeling like work.

When the mission is clear, vacation becomes optional.

The grind becomes a choice, not a burden.

That’s the difference between building something you tolerate and building something you can’t stop thinking about.

#founder #startup #entrepreneur #business #ceo

Allison Baum Gates is a General Partner at SemperVirens VC, an early-stage venture capital firm investing in healthcare, fintech, and enterprise SaaS. An experienced technology investor, author, and speaker, she has raised hundreds of millions of dollars from global LPs and backed more than 70 companies—with nine unicorns, 24 exits, and 10 board roles among them. Previously, she co-founded Fresco Capital, invested at Trinity Ventures, and was an early team member at General Assembly, acquired by Adecco for $413 million. A Harvard graduate and former Goldman Sachs trader, Allison has lived and worked across five countries, lectures at Columbia Business School and UC Berkeley-Haas, and is the author of Breaking into Venture (McGraw-Hill, 2023), a guide to understanding and entering the VC industry.

Topics: 

- Pattern recognition at scale: what actually separates durable venture returns from hype cycles

- Building and managing institutional LP relationships across geographies and fund vintages

- Board dynamics, power, and governance in venture-backed companies from seed to exit

#VentureCapital #InstitutionalInvesting #BoardGovernance #StartupScale #SmartVenturePodcast

Allison Baum Gates, SemperVirens GP on Future of Work & HR Tech

How to land a whale 🐳 in B2B sales.

You don’t chase it.
You don’t rush it.
You don’t scare it away.

Whale watching made this painfully obvious.

The biggest deals surface when buyers are ready — not when your quarter needs help.

#B2BSales #EnterpriseSales #Startups #Founders #GoToMarket

I've chatted with 200+ AI founders backed by a16z, Sequoia, Lightspeed and other top VC funds on my podcast and at my dinners. Here's what actually happens in 2026.

I'm joining Matt Wolfe (800k+ YouTube subs), Jeremiah Owyang (GP at Blitzscaling Ventures), and Chappy Asel from The AI Collective for a forecasting session where we're actually putting money down.

What we're betting on:
→ Who's the best AI lab by Dec 31st: OpenAI, Anthropic, Google, or xAI?
→ Does anyone claim AGI in 2026?
→ Will AI close a $50k+ deal on its own?
→ Can AI actually ship code without breaking everything?
→ What are we all missing?

Here's what I know: The gap between AI demos and actual revenue is massive. 

Every founder I talk to is building agents. Almost nobody's buying them at scale yet.

That changes in 2026. Or it doesn't.

Hosted by our friends at The AI Collective (150k+ AI builders), Kalshi (regulated prediction markets), and Roam (AI-powered virtual HQ).

See you there.

#AI #AIAgents #AGI #TechPredictions #Startups

David Zeng is Co-Founder and CTO of Beacons AI, the Y Combinator-backed all-in-one platform powering 9M+ creators with AI-native tools for link-in-bio pages, websites, email marketing, ecommerce, and monetization across Instagram, TikTok, YouTube, and more—helping solopreneurs turn brand deals, affiliates, and digital products into sustainable businesses without tech headaches. A Stanford PhD in signal processing and machine learning whose medical imaging research deployed globally in hospitals, David previously led ML at Azumio (launching Calorie Mama AI) and interned on computer vision at Google, bringing hardcore AI engineering to the $250B creator economy where Beacons handles unique creator mixes on every major US social network.

Topics:
  - Using ML signal detection to spot viral patterns before platform algorithms react.
 - AI link-in-bio 3x's conversions – predicts TikTok/IG/YouTube audience overlap
 - Why the creator economy needs AI-native tools, not more dashboards

 #CreatorEconomy #SaaS #Startups #YC #TechInvesting

David Zeng, Beacons CTO on AI Tools for Creator Economy

Joseph Ros is a Partner and General Manager at Entrepreneur First(EF), the pioneering global platform that invests in exceptional individuals before they have an idea or co-founder. Based in San Francisco, Joseph has backed early-stage technology companies across AI, biotech, robotics, hardware, and climate tech in markets including Singapore, India, Europe, and North America. At EF, he leads talent investing and follow-on capital while driving EF’s global pipeline that connects top technical talent from Europe and India to Silicon Valley. Before joining EF, Joseph was a founder and self-taught engineer, building and scaling consumer web products that reached millions of users across industries like gaming, legaltech, and edtech.

Topics: 
- Talent-first investing: Why backing individuals before ideas produces outlier companies
- How EF evaluates founders at day zero (signal, grit, and technical edge)
- Building global founder pipelines: Europe & India as the next AI power centers

#VentureCapital #TalentInvesting #EarlyStageVC #AIStartups #GlobalFounders

Joseph Ros, Partner at EF on Talent-First Investing & Global Scale

Distribution for startups 101.

Stripe didn’t buy growth — they embedded into platforms that already had users.

#startups #founders #distribution #growthstrategy

entering my villain era 😈

#2026 #founder #ceo

🎉 Week 102 Recap — Venture with Grace  

Week 102 explored cutting-edge AI infrastructure, VC investment strategies, GTM mastery for SaaS, causal AI innovations, and usage-based billing revolutions — unpacking commercialization, diligence, scaling, and growth in tech.

Week 102 lineup:

Deepak Prasad, Qualcomm Director: Qualcomm's US tech deals, long-term technical advantage, cloud-to-edge diligence

Priya Ramachandran, Foster Ventures Founder: GTM for international SaaS, proving PMF for cross-border founders, operator investor eval

Ray Wu, Alumni Ventures Managing Partner: Global AI & SaaS investing, corporate venture lessons from HP & Cisco, building startups across markets

Abby Kearns, former CTO of Alembic Technologies on AI and OpenSource: Modernizing Puppet to cloud-native, causal AI for marketing ROI, scaling global eng teams

Scott Woody, Metronome CEO: Usage-based billing as core infra, scientific modeling in SaaS, Dropbox-scale lessons for startups

Week 102 delivered battle-tested insights on turning research into VC-backed reality, diligencing edge tech, and fueling SaaS growth amid 2026 shifts. The big theme: Builders and investors are redefining infrastructure for an AI-driven world.

See you live next week for more exciting episodes! 👋

#VentureWithGrace #AI #startups #founders #vc

Vignesh Ravikumar is a Partner at SIERRA Ventures. Vignesh Ravikumar joined Sierra Ventures in 2013 and focuses on investments in Enterprise SaaS, Vertical SaaS, and Digital Health/Healthcare IT. Vignesh has a background in M&A transactions for enterprise software companies, having worked at AGC Partners, a Boston-based investment bank. Vignesh holds a BS in Management Science (cum laude) and a Minor in Math from UC San Diego. 


Topics: 
- Underwriting AI-heavy SaaS when infra, pricing, and competition shift
- Pricing and packaging playbooks for AI-native SaaS at seed/Series A
- Vertical SaaS 2.0: deep workflow, compound products, and moats

#VentureCapital #EnterpriseSaaS #VerticalSaaS #DigitalHealth #HealthcareIT

Vignesh Ravikumar, Dhanush Ram and 5 other attendees

Vignesh Ravikumar, Sierra Ventures Partner on Enterprise & Vertical SaaS

Aaron Cannon — CEO of Outset — on Venture with Grace, sharing how AI is reshaping the pace and depth of research.

Aaron walked through how this approach unlocks faster understanding without sacrificing nuance, helping teams learn more, sooner, and make better decisions with confidence.

Episode is live now — a compelling look at how AI can accelerate research and insight at scale. Link in Bio.

#AIResearch #UXResearch #ProductDiscovery #QualitativeResearch #QuantitativeResearch

Scott Woody is Co-Founder and CEO of Metronome, the leading usage-based billing platform empowering SaaS companies to model flexible pricing strategies, iterate rapidly without engineering bottlenecks, and turn billing into a growth engine amid 2026's shift from seats to consumption models. With prior stints as CTO at Metronome since 2019 and Director of Engineering at Dropbox where he scaled core infrastructure for 12 million+ users, Scott brings hands-on builder credentials from co-founding Foundry Hiring—an ultra-simple ATS that handled full-stack from marketing to code. A Stanford grad whose computational biology research spanned protein folding simulations, DNA mutations, and motor protein assays, he bridges academic modeling rigor with enterprise software at scale, having engineered Dropbox's evolution from startup to public giant before tackling SaaS monetization's biggest pain point.

Topics
- Why usage-based billing is becoming core infrastructure, not a finance feature
- How a scientific modeling background shaped a SaaS infrastructure founder
- Lessons from Dropbox-scale systems applied to early-stage startups

#UsageBasedBilling #SaaSGrowth #PricingInfrastructure #FounderInsights #BuildInPublic

Scott Woody, Metronome CEO on Usage-Based Billing & SaaS Growth

How to build distribution for your startup (without burning cash).

Nike didn’t hire Kim Kardashian. They partnered with her company SKIMS. 

Here’s how. Follow me so your startup doesn’t die.


#startups #founders #distribution #businessstrategy #entrepreneurship

Aaron Jacobson  — Partner at New Enterprise Associates (NEA) — on Venture with Grace, spotlighting the next major frontier in cybersecurity.

As devices, applications, and data become more secure, identity is emerging as the critical layer left to solve. With agents operating across systems, knowing who has access — and proving it in real time — matters more than ever.

Aaron shared why identity sits at the center of modern security and how real-time verification will define the next generation of protection.

Episode is live now — a sharp conversation on cybersecurity, identity, and what comes next. 

#Cybersecurity #Identity #EnterpriseSecurity #VentureCapital

Howard Wright — VP at NVIDIA — on Venture with Grace, sharing a simple but powerful leadership habit.  

Being fully present when someone is speaking sounds obvious, but in a world full of notifications and constant distraction, it’s a rare skill. Howard framed deep listening as a sign of respect — and of quiet confidence.  

He shared how leaders who truly listen build stronger trust, make better decisions, and lead with humility.  

Episode is live now — a thoughtful reminder on presence, leadership, and the power of listening.

#Leadership #ActiveListening #Management #ExecutivePresence

Lior Susan  — founder & CEO of Eclipse — on Venture with Grace, sharing a framework for spotting the next wave of disruption.

To find industries ready for transformation, Lior looks bottom-up: study how work actually gets done, layer in the macro forces at play, and examine the technologies powering the ecosystem today.

He pointed to how e-commerce reshaped logistics as a reminder that when technology meets the right market conditions, entire industries can change — raising the question of what’s next.

Episode is live now — a thoughtful conversation on innovation, venture investing, and identifying inflection points.

#VentureCapital #Innovation #Disruption #EmergingTech

Kyle Thomas

Went from cubicle data entry to Uber Employee 250 & Startup Exec | Helping you land your career-accelerating role in less than 90 days | Founder & CEO of UpEmployment Accelerator

When it comes to startup job seeking everyone wants to be an early employee at a unicorn 🦄 & earn millions 💸.

But what's the secret to landing those opportunities? 

Here's a hint...

They don't come from the "traditional job search".

When I was job seeking I had no idea what I was doing, but with experience and research, I found ways to stack the deck in your favor.

That's what led me to land a job as Uber's 250th employee. 

After Uber, it's what led me to a VP role with a $100k salary increase at a Y-Combinator startup.

That's why I built Early.

Do you have amazing experience & want to take the next step to accelerate your career in a startup, but not sure where to start?

I wished that someone had a playbook for how to do that. 

It didn't exist, so I created it.

The Early Accelerator gives highly talented job seekers a complete playbook for how to land your next dream role plus accountability & a community to guide you along the way.

The program is designed to allow you to:
- 10x your job hunt efficiency
- Know where you want to go
- Build your personal brand
- Know the salary and equity you command
- Create a system to generate connections & opportunities
- Generate 100x more warm network connections
- Leverage repeatable frameworks
- Get in a peak performance state
- Create unwavering confidence
- Get to your dream role

Despite the challenging job market, we have seen incredible results.
↳ Average job searches lasting ~3 months (90 days vs US avg of 5 months).
↳ >$200k in salary increases.
↳ >$800k in equity increases.
↳ Total compensation increases of over $1M.
↳ Advancements from Manager to Department Head.
↳ Major career jumps from VP to the C-Suite.

I formalized the proven system into an easy-to-execute framework that anyone can use to land their dream job.

My mission is to help millions live extraordinary lives by accessing opportunities that change their careers forever.

You deserve to work in a job that lights you up, pays you what you are worth, and accelerates you toward your vision of your dream future.

Let's go get you that job!

So, D.M 📩 me here or email me at kyle@BeEarly.com today so we can accelerate your startup career the right way.

Stop wasting time applying to every company where you meet the minimum qualifications and learn our proven way to land your dream job!

P.S. If you're a startup job seeker looking to cut your job search in half, outperform over 95% of other candidates, and land a top startup job, click the link in my Featured Section and apply today!

Founder

I take groups of people from A to Z in their job search so they can land their dream job without applying online.

These methods took me from cubicle data entry to a job as Uber employee 250 and from unemployed to startup executive. I'm not special, I can teach you to do the same!

More than 80 startups became unicorns in 2025.

Here are 20 that are hiring 👇

1) Reflection AI 
• Stage: Series B
• Recent Raise: $2B
• Recent Valuation: $8B
• Employees: 60
• Hiring In: SF, NYC, DC, LDN

2) Lila Sciences
• Stage: Series A
• Recent Raise: $235M
• Recent Valuation: $1.26B
• Employees: 195
• Hiring In: CAM, SF, LDN

3) Tempo 
• Stage: Series A
• Recent Raise: $500M
• Recent Valuation: $5B
• Employees: 50
• Hiring In: SF, NYC, Remote

4) NewLimit 
• Stage: Series B+
• Recent Raise: $45M
• Recent Valuation: $1.6B
• Employees: 43
• Hiring In: SF

5) LangChain
• Stage: Series B
• Recent Raise: $125M
• Recent Valuation: $1.25B
• Employees: 136
• Hiring In: SF, NYC, BOS, DAL, MSP, CHI, LDN, Remote

6) ShopMy
• Stage: Series B
• Recent Raise: $70M
• Recent Valuation: $1.5B
• Employees: 140
• Hiring In: NYC, LA, AUS, Remote

7) Substrate
• Stage: Seed
• Recent Raise: $100M
• Recent Valuation: $1B
• Employees: 50
• Hiring In: SF

8) Fireworks AI 
• Stage: Series C
• Recent Raise: $250M
• Recent Valuation: $4B
• Employees: 148
• Hiring In: NYC, SM

9) Modal 
• Stage: Series B
• Recent Raise: $87M
• Recent Valuation: $1.1B
• Employees: 14
• Hiring In: NYC, SF, Remote

10) Gamma 
• Stage: Series B
• Recent Raise: $68M
• Recent Valuation: $2B
• Employees: 52
• Hiring In: SF, LA, Remote

11) MainFunc
• Stage: Series B
• Recent Raise: $275M
• Recent Valuation: $1.25B
• Employees: 40
• Hiring In: PAO

12) Luma AI 
• Stage: Series C
• Recent Raise: $900M
• Recent Valuation: $4B
• Employees: 24
• Hiring In: PAO, LA, NYC, LDN, Remote

13) Harmonic 
• Stage: Series C
• Recent Raise: $120M
• Recent Valuation: $1.45B
• Employees: 37
• Hiring In: PAO

14) Curative
• Stage: Series B
• Recent Raise: $152.55M
• Recent Valuation: $1.3B
• Employees: 2800
• Hiring In: AUS, DAL, FL, Remote

15) Heven AeroTech
• Stage: Series B
• Recent Raise: $100M
• Recent Valuation: $1B
• Employees: 67
• Hiring In: WA, VA

16) Kalshi 
• Stage: Series E
• Recent Raise: $1B
• Recent Valuation: $11B
• Employees: 75
• Hiring In: NYC, Remote

17) Unconventional AI
• Stage: Seed
• Recent Raise: $475M
• Recent Valuation: $4.5B
• Employees: 15
• Hiring In: PAO

18) Serval
• Stage: Series B
• Recent Raise: $74.82M
• Recent Valuation: $1B
• Employees: 50
• Hiring In: SF

19) Lovable
• Stage: Series B
• Recent Raise: $425.01M
• Recent Valuation: $6.6B
• Employees: 120
• Hiring In: STO, BOS, SF, LDN, Remote

20) K2 Space Corporation 
• Stage: Series C
• Recent Raise: $250M
• Recent Valuation: $3B
• Employees: 200
• Hiring In: LA, Remote

I dropped the final 5 in the comments below.

📆 Come back next Monday for another list of top startups looking for their next great hires.

Give me a follow, (Kyle Thomas) so you don’t miss it.

Go get that job and build something awesome 💪

♻️ Share this to help startup job seekers find a new role.

I Teach Ambitious Startup Job Seekers How To Land Career-Accelerating Roles at World-Changing Startups | “De-Risk” the Search w/ Proven Methods & Investor-Grade Data | Apply to our Startup Job Search Accelerator Below

If you’re job-searching in 2026, start here: 

These are my top 7 most useful posts of the year, distilled into one list.

1. Interviews are won in advance

The separation is in the preparation.

Use AI to simulate interviews, identify doubts, and rehearse answers out loud.

The people who practice the most win the most.

Post: https://dub.sh/2syNUyQ

2. Top candidates don’t just apply, they make the team feel something

They research deeply, understand the product, the priorities, and the people.

They walk into the interview already feeling like part of the team.

Post: https://dub.sh/Ldadro6

3. Scrolling job boards is fake work

Build an AI-driven newsfeed that surfaces roles, angles, insights, and outreach opportunities every morning. 

Replace doomscrolling with daily momentum.

Post: https://bit.ly/K2sVVEX

4. Measure your outreach

Most people underestimate the numbers.

If your response rate is ~10%, you may need 300–800 messages to land 1 offer.

Don’t look at the numbers as discouraging. Use them to drive commitment to action.

Once you see the math, you can stop taking rejection personally.

Post: https://dub.sh/PkyI6K2

5. If your job search has stalled, you haven’t failed - you’ve stopped experimenting

Most people repeat the same 3 tactics and expect new results.

Try 50 micro-experiments instead.

Track what works, adapt, iterate.

Post: https://dub.sh/2YXxqoT

6. Creativity wins, sloppiness loses

Creative applications stand out, but a lack of attention to detail kills your chances instantly.

One Early member got an offer after spending $11 on a bus ticket to record a personalized video for a startup.

Post: https://dub.sh/soykHKH

7. Momentum > motivation

Job searches get overwhelming.

Build micro-habits: move your body, send the message, ask for help, revisit your “why.”

Progress compounds.

Post: https://dub.sh/NmDNmpP

Yes, these were my top posts of the year.

But they were also the lessons that actually moved people into new roles, new industries, and new opportunities.

If you found this helpful, follow me, Kyle Thomas.

2026 is going to be packed with even more value-dense, practical, and brutally honest job search frameworks to help you land the role you want.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

AI should make your job search faster - not soulless.

I was chatting with a hiring manager of a rapidly growing Series C startup about a position she was looking to fill.

This company has: 

- $78M raised to date
- A>$450M valuation
- Multi-time founders with successful exits
- Top VC investors

“We generally look for a cover letter of someone really saying why they’re interested in [COMPANY]. I reject people who have AI-written cover letters. It’s an initial screener of whether or not this person cares enough to be here.”

This quote is word-for-word from the conversation.

AI is one of the most powerful tools in your job search, but only if you use it properly.

Used Well: It helps you find roles faster, prepare smarter, research deeper, and articulate your strengths clearly.

Used Poorly: It makes you look generic, lazy, and un-hirable.

Here are the dos and don’ts of using AI in your job search so you get the speed without losing the human connection.

𝗔𝗜 𝗗𝗼’𝘀:

- Use AI to scrape job boards to find roles and score them against your ideal job
- Use AI to research companies, founders, product roadmaps, and competitors
- Let AI help you structure your stories, case studies, and portfolio work
- Let AI help you draft thinking (think bullets), not your final messaging
- Use AI to simulate interview scenarios and rehearse answers
- Ask AI to identify interviewer doubts based on your résumé

𝗔𝗜 𝗗𝗼𝗻’𝘁𝘀:

- Don’t publish raw AI output without editing it heavily in your voice
- Don’t submit AI-written cover letters or outreach messages
- Don’t think AI auto-apply bots will land you a great role
- Don’t outsource your thinking, only your processing
- Don’t use generic prompts with no context
- Don’t rely on AI as your personality

AI is an amazing co-pilot. 

But it is far from being your replacement.

Used well, it helps you be more efficient and speeds up mundane tasks.

But used poorly, it’ll ruin your search and remove you from opportunities or relationships that could have dramatically accelerated your career.

Don’t let laziness be your downfall.

Use it to remove the mundane, think sharper, prepare smarter, and move faster than other candidates - not to copy-paste your way through the process.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

Burnout isn’t caused by work.

It’s caused by the 𝘸𝘳𝘰𝘯𝘨 work.

Most people think they’re exhausted because they’re overworked.

But the truth is far simpler:

When your job drains you, 4 hours feels like 14.

When your job energizes you, long days feel light.

During my career, I’ve lived both versions.

I started out working in a cubicle data-entry job.

Clocked in at 9 am. Clocked out at 5 pm.

And I was dead tired before, during, and after work.

Not because it was “hard.”

But because it gave me nothing back.

Then I joined Uber in the early days.

I’d get in at 8 am and leave at 11 pm some nights -

and I had 𝘮𝘰𝘳𝘦 energy than I’d ever had in my life.

Same body. Same brain. Different work.

Here’s what nobody tells you:

Good work gives energy, but bad work steals it.

And your body knows the difference long before you admit it.

If you wake up every day needing caffeine just to feel human…

it’s not a coffee problem.

It’s a career problem.

You deserve work that fills your cup, not empties it.

When did you realize an old role was draining you? 
Drop it below 👇🏻 Lets talk about it.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

If I had to start from scratch, I wouldn’t touch my résumé.

This is what I’d do instead 👇🏻

After coaching hundreds of startup candidates, the fastest path into a great startup role always follows the same shape:

Less résumé polishing.

More relationship building, clarity, and conversations.

Here’s exactly how I’d structure my job search, week-by-week, if I was starting today:

𝗪𝗲𝗲𝗸 𝟭 - I’d prep for rejection & get clear on what I want

→ Reset my mindset and limiting beliefs
→ Expect rejection (it’s part of the game)
→ Define what I want & the exact role characteristics I’m targeting

Clarity comes before momentum.

𝗪𝗲𝗲𝗸 𝟮 - I’d build confidence

→ Benchmark comp (what I could earn)
→ Refine my “About me” story (my hero’s journey)
→ Review my highlight reel of accomplishments
→ Refresh LinkedIn & résumé, so they speak directly to those roles
→ Build my target startup list

Confidence is the second step in a strong job search foundation.

𝗪𝗲𝗲𝗸 𝟯 - I’d create opportunities instead of waiting for them

→ Start with my warm network
→ Then cold outreach to people in target companies
→ Ask real questions, share interests, and engage publicly on LinkedIn
→ Show up where they hang out (online & in person)
→ Look for ways to deliver even small amounts of value

Early connection is more powerful than applications.

𝗪𝗲𝗲𝗸 𝟰 - I’d apply & prep before interviews get booked

→ Apply to companies that match my ideal job description
→ Never “just apply”, pair it with outreach & value
→ Do deep research on the company (yes, using AI)
→ Practice stories out loud, identify gaps, prep examples

Interview prep is 10x easier when you do it before you’re stressed.

𝗪𝗲𝗲𝗸 𝟱 - I’d follow up like a top candidate

I’d send value deliverables:

→ Insights
→ 30-60-90 ideas
→ Product thoughts
→ Short frameworks
→ Connections to my network

Be politely persistent.

Show excitement, agency, & what you’re capable of.

𝗪𝗲𝗲𝗸 𝟲 - I’d convert the momentum

→ By now, I should be in conversations.
→ I’d prepare for each one like it’s my last.
→ I’d demonstrate excitement + impact with examples, case studies, past wins, and mini-deliverables.

𝗪𝗲𝗲𝗸 𝟳 - I’d evaluate & refine

→ Track what worked.
→ Track what didn’t.
→ Update messaging.
→ Repeat what performed well.

Consistency compounds.

𝗪𝗲𝗲𝗸 𝟴 - I’d keep going

Applications + outreach + value delivery.

This is the system that lands outsized opportunities.

If you follow this 8-week plan, your job search becomes a system, not chaos.

This is the exact roadmap I’ve seen help hundreds of candidates land roles at companies they once thought were out of reach.

Commit to it. Stay consistent. Track it. Improve faster than 90% of job seekers.

📌 Save this post - you’ll want it when your next interview loop starts.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ Want clarity on your job search? DM me to learn how Early can support you.

What to join a startup with a good chance of success?

Join a founder with a prior successful exit.

The founders of these 20 Series B startups have already had a successful exit. 

𝗧𝗵𝗲𝘆'𝗿𝗲 𝗮𝗹𝘀𝗼 𝗵𝗶𝗿𝗶𝗻𝗴 𝗻𝗼𝘄!

This week I pulled a list of startups that:
• Are backed by top investors
• Raised a Series B 4-12 months ago
• Have a founder with a previous exit
• Are growing headcount faster than any other Series B

If you're looking to join a Series B startup that's rapidly hiring, check the careers pages for these startups below.

𝘒𝘦𝘺: 𝘊𝘰𝘮𝘱𝘢𝘯𝘺: 𝘓𝘢𝘴𝘵 90-𝘥𝘢𝘺 𝘯𝘦𝘸 𝘩𝘪𝘳𝘦𝘴, # 𝘰𝘧 𝘢𝘤𝘵𝘪𝘷𝘦 𝘰𝘱𝘦𝘯 𝘳𝘰𝘭𝘦𝘴

 1. XBOW: 53 new hires, 38 openings roles
 2.  Fay Nutrition: 46 new hires, 5 open roles
 3.  Together AI: 38 new hires, 42 open roles
 4.  Levelpath: 32 new hires, 30 open roles
 5.  Monarch: 31 new hires, 7 open roles
 6. Sprinter Health: 27 new hires, 24 open roles
 7.  Savvy Wealth: 27 new hires, 16 open roles
 8.  Endor Labs: 22 new hires, 16 open roles
 9.  WorkWhile: 17 new hires, 19 open roles
10.  Tessell: 17 new hires, 15 open roles
11.  Tabs: 17 new hires, 23 open roles
12.  NetBox Labs: 16 new hires, 14 open roles
13.  Sentra: 14 new hires, 7 open roles
14.  Arena: 13 new hires, 7 open roles
15.  The Bot Company: 12 new hires, 14 open roles
16.  Archive: 11 new hires, 4 open roles
17.  GreenLite: 11 new hires, 11 open roles
18.  Aalo Atomics: 11 new hires, 22 open roles
19.  Mojo Vision: 10 new hires, 1 open role
20.  Omni: 9 new hires, 18 open roles

Go get that job and build something awesome 💪
____________

📆 Come back next Monday for another list of top startups looking for their next great hires.

Give me a follow, (Kyle Thomas) so you don’t miss it.

♻️ Share this to help startup job seekers find a new role.

Oh... and 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗹𝗼𝗼𝗸𝗶𝗻𝗴 𝗳𝗼𝗿 𝘆𝗼𝘂𝗿 𝗻𝗲𝘅𝘁 𝘀𝘁𝗮𝗿𝘁𝘂𝗽 𝗿𝗼𝗹𝗲, 𝘀𝗵𝗼𝗼𝘁 𝗺𝗲 𝗮 𝗗𝗠. 

We just had someone join our program and land a job at a top Series B startup in 𝗷𝘂𝘀𝘁 𝟮𝟳 𝗱𝗮𝘆𝘀.

For the love of all that is good, stop clicking “Easy Apply”.

I get it, it makes you feel productive.

You’re tired, you’re stressed, and hitting one button gives you that tiny dopamine hit that says, “At least I did something today.”

But here’s the truth that no one wants to hear:

The Easy Apply button is a trap.

It feels like progress, but it puts you in the same pile as 1,200 other candidates, most of whom also didn’t read the job description.

And with AI tools now submitting 50+ applications per minute, you’re competing in a volume game you simply cannot win.

If you want to work in startups, spamming the Easy Apply button is the worst strategy you can choose.

Startups don’t hire people who blend in.

They hire people who stand out.

The ones who are excited, passionate, sharp, opinionated, action-oriented, and creative.

And you can only show those qualities by being intentional.

𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝘄𝗼𝗿𝗸𝘀:

↳ Instead of 40 easy applies → pick 5 roles you genuinely want.

↳ Instead of spraying resumes → deeply research the company, product, and team.

↳ Instead of hoping the algorithm boosts your application → message the hiring manager, founder, and anywhere from 5-20 people on the team.

↳ Instead of generic cover letters → send a short, sharp note about why you’re excited and exactly how you’ll add value, and include a link to a Loom video of you speaking about why you’re a good fit.

↳ Instead of waiting → build one thing that proves you can do the role.

In a world where applying takes three seconds or less, effort and “human-ness” are the differentiators.

When you apply intentionally, people notice.

When you reach out like a human, people respond.

When you make it clear you understand the role and the company, people take you seriously.

Easy Apply helps you feel busy, but it’s intentionality that gets you hired.

If you can replace 60 minutes of scrolling with 60 minutes of targeted outreach, research, and personalized messages, you will outrun 99% of candidates in this market.

Trust me when I say - your next role 𝘞𝘖𝘕’𝘛 come from a button.

It’ll come from clarity, effort, and showing up like someone a founder or executive would actually want to hire.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

Most job searches fall apart because everything happens at once:

Applications, outreach, interviews, self-doubt, urgency

Landing a start-up role isn’t about having the best-looking résumé.

It’s about running a 𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲𝗱 𝘀𝘁𝗮𝗿𝘁-𝘂𝗽 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝗮𝗻𝗱 𝗳𝗼𝗰𝘂𝘀𝗶𝗻𝗴 𝗼𝗻 𝘁𝗵𝗲 𝗶𝗺𝗺𝗲𝗱𝗶𝗮𝘁𝗲 𝗺𝗼𝘀𝘁 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁 𝘁𝗵𝗶𝗻𝗴.

Often members join Early with no system… just scattered effort.

The people who succeed in landing great startup roles don’t necessarily work harder. 

They follow a 𝗰𝗹𝗲𝗮𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝗽𝗹𝗮𝗻, broken into stages.

They know when to get clear on the role they want. When to build momentum through outreach and conversations. And when to convert trust into offers.

That’s exactly what the 𝟯𝟬–𝟲𝟬–𝟵𝟬 𝗱𝗮𝘆 𝘀𝘁𝗮𝗿𝘁𝘂𝗽 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝗽𝗹𝗮𝗻 is designed to do.

It turns your job search from:

 • scattered → focused
 • reactive → intentional
 • emotional → manageable

Once you have a system, you stop asking:

“Am I doing enough in my job search?”

And start asking:

“Am I doing the right thing 𝘢𝘵 𝘵𝘩𝘪𝘴 𝘴𝘵𝘢𝘨𝘦?”

That shift is what helps candidates land startup roles faster without burning out or second-guessing every move.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

30 60 90 Day Plan

Comp can gets the offer signed.
Culture decides whether they sprint or quietly plan their exit.

Here’s the truth most founders and startup hiring managers learn the hard way:

You can’t buy anyone’s commitment.

You can’t bonus your way into long-term loyalty.

And you definitely can’t “culture-deck” your way out of a bad environment.

At early-stage Uber, none of us were printing money.

We had equity we hoped would be worth something, but… it wasn’t worth anything at the time. Nor did we have any guarantee the whole thing would work out.

And we definitely weren’t sitting on giant salaries.

I made $65k in my first role at Uber in 2013. That was an 85% increase over my prior role and ~$95k in today’s dollars (I thought I was RICH!).

There were people with degrees from Harvard and Stanford and masters degrees from top programs who were earning similar amounts.

But despite all that, we were willing to run through walls for the company.

Why?

Because we believed in the mission, the founder, and the product.

People don’t sprint because the comp is great, they sprint because the environment makes them want to show up with everything they’ve got.

𝐂𝐮𝐥𝐭𝐮𝐫𝐞 𝐢𝐬:

→ Whether the people around them are high caliber A players
→ Whether people are safe to speak honestly and critically
→ Whether there is transparency with data and progress
→ Whether the people like to see each other every day
→ Whether effort and impact are seen and recognized
→ Whether people are given autonomy to do their job
→ Whether the mission actually means something
→ Whether the team feels trusted
→ Whether credit is shared

Compensation gets all the attention.

But CULTURE gets outsized performance.

And if someone leaves because of a bad culture, guess what?

They’re gone for good.

There’s no counter-offer that fixes “I don’t want to be here anymore.”

In fact, I’ve heard SO many times, “You couldn’t pay me enough to go back there.”

But if they leave for money, and the culture was strong?

They’ll think about coming back.

I’ve seen quite a few of my early Uber colleagues leave after 4+ years at the company, only to return because they loved the culture.

People always remember where they did their best work.

📌 Save this post - you’ll want it when your next interview loop starts.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ Want clarity on your job search? DM me to learn how Early can support you.

You’re treating LinkedIn like a social media profile.

It’s not.

Your LinkedIn page is a sales landing page and LinkedIn is the search engine.

Here’s how to rank higher in the job search in just 1 hour.

1. 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂𝗿 𝗵𝗲𝗮𝗱𝗹𝗶𝗻𝗲, 𝗶𝘁 𝗱𝗼𝗲𝘀 𝟴𝟬% 𝗼𝗳 𝘁𝗵𝗲 𝘄𝗼𝗿𝗸.

If it’s vague, generic, or stuffed with buzzwords, you won’t appear in relevant searches. 

And if you do, they won’t know what the heck you do or how you fit in their org.

In 3 seconds, they should be able to tell:

 • Who you are
 • What you do
 • The results you drive
 • Who you drive them for

If that’s not the case with your headline today, change it.

Think: “Senior Startup Operations Leader | Scaling Systems, People & Processes Leveraging AI | Led the operational launch of multiple marketplaces from $0 - $500M ARR.”

2. 𝗡𝗲𝘅𝘁, 𝗳𝗶𝘅 𝘆𝗼𝘂𝗿 𝗔𝗯𝗼𝘂𝘁 𝘀𝗲𝗰𝘁𝗶𝗼𝗻.

Lead with who you are today and your mission, then back it up with proof.

Use keywords and case studies that founders and recruiters already search for: operations, product, GTM, strategy, growth, project management, AI, SaaS - whatever applies to the work you want.

(Hint: These are found in the JD, so create a long list of JDs and extract the keywords and case studies using an LLM)

Also, inject something personal. Show that you’re an actual human with real interests.

Being “passionate about process optimization“ is not a personality.

3. 𝗧𝗵𝗲𝗻 𝗴𝗼 𝗿𝗼𝗹𝗲 𝗯𝘆 𝗿𝗼𝗹𝗲, 𝗽𝘂𝗹𝗹 𝗼𝘂𝘁 𝘁𝗵𝗲 𝗾𝘂𝗮𝗻𝘁𝗶𝗳𝗶𝗲𝗱 𝗮𝗰𝗵𝗶𝗲𝘃𝗲𝗺𝗲𝗻𝘁𝘀, 𝗮𝗻𝗱 𝘀𝗵𝗼𝘄 𝗽𝗿𝗼𝗼𝗳.

Search engines love clarity.

Recruiters love impact.

Your job is to give both.

Attach links to documents, PR releases, anything that shows you actually did what you say you did.

4. 𝗔𝗳𝘁𝗲𝗿 𝘁𝗵𝗮𝘁, 𝘂𝗽𝗱𝗮𝘁𝗲 𝘆𝗼𝘂𝗿 𝘀𝗸𝗶𝗹𝗹𝘀.

Not 60 random ones.

The top 60 that map directly to the job you want.

Some recruiters use these in their search filters, but most candidates ignore them entirely.

(Hint: Remember where I told you to find these skills? In the JDs)

5. 𝗙𝗶𝗻𝗮𝗹𝗹𝘆, 𝗮𝗱𝗱 𝗮 𝗰𝗿𝗲𝗱𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝘀𝗶𝗴𝗻𝗮𝗹.

Pin a post that proves your thinking, showcases a win, or highlights a perspective that matters in your niche.

You could start a newsletter, a podcast, or share a badass proof of work example.

It’s the fastest way to turn a profile view into an outreach message.

Most people treat LinkedIn like a digital resume without realizing that founders, recruiters, and operators treat it like Google.

They search for skills, functions and people who signal credibility in the first 3 seconds.

LinkedIn itself has changed its search functionality to be more conversational and function like a search engine instead of a database with filters.

The people who win on LinkedIn aren’t the loudest, they’re the most discoverable.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

“Do I actually want this role?”

That’s the question you need to answer honestly if you resent the pre-job assignment.

I’m talking about the case studies, presentations, and work samples as a part of the hiring process.

The hiring team didn’t create a pre-job assignment as a thoughtless hoop to jump through just to make the process harder.

It’s a trailer for the movie.

And if you hate the trailer… you’re going to hate the movie.

Assignments are the best way for the team to get an idea of what it would actually feel like to work with you.

They’re also a great way for you to stand out in the process.

They’re also a great gut check of how much you want to work there.

They show you:

 • How the team thinks
 • What problems you’ll work on
 • Whether the work energizes or drains you
 • Whether you’d enjoy doing this every day, not just once

And yes - some people argue candidates “shouldn’t have to do pre-work before speaking to a hiring manager.”

I disagree 100%.

If you want the job, you’ll do the work.

If you resent the work, you don’t want the job.

Simple.

It may sound harsh, but it shouldn’t.

Take for example Caleb Ralston. 

He has helped build the personal brands for some of the largest founder-led brands out there. 

He was recently hiring for YouTube editors, and do you know what the process looked like?

YouTube editor TRYOUTS over the course of 4 days.

Candidates needed to sign up, were sent the raw video/audio files, and had four days to edit and submit their final video edit.

No interviews before the exercise, just “show me what you got”.

Hundreds of people signed up and did the free work for the opportunity to work with one of the best out there.

And that’s the thing, if you’re not willing to do it, in this market (and in any market at most top companies), there will be people who are more than willing to do the free work.

If you find yourself procrastinating, irritated, or indifferent, that’s your signal not to push harder… but to walk away.

But if you find yourself getting curious, going deeper, losing track of time…

That’s a signal that you should lean in.

That the role might actually be right for you.

That this is work you'll enjoy, not just endure.

The pre-job assignment is a preview of the next chapter of your career.

If you hate the trailer, don’t buy the movie ticket.

If you love it, that’s your green light to go hard.

A quick aside: I know people abuse these exercises but that’s not the norm. I spoke with a new grad last week who worked 80 hours a week for two weeks for a founder on an “exercise” to build them a product. The founder even asked her to work on Christmas day. After the two weeks they shared the salary and equity and it was far lower than market rate.

So do people abuse exercises, yes. But in my experience they’re few and far between. The best companies will run you through thoughtful exercises and the exercises and “free work” are an incredible way to stand out.

Most people sabotage their startup job search by misreading silence.

Early in my career, I was wary of being annoying.

If I had a good conversation with someone and they said, “Happy to help” or “Let me look into that”, I’d leave it there.

Then a week would pass. Then two.

And then... I’d start to spiral.

 • 𝘚𝘩𝘰𝘶𝘭𝘥 𝘐 𝘧𝘰𝘭𝘭𝘰𝘸 𝘶𝘱?
 • 𝘞𝘩𝘢𝘵 𝘪𝘧 𝘵𝘩𝘦𝘺 𝘧𝘰𝘳𝘨𝘰𝘵?
 • 𝘞𝘩𝘢𝘵 𝘪𝘧 𝘐 𝘭𝘰𝘰𝘬 𝘥𝘦𝘴𝘱𝘦𝘳𝘢𝘵𝘦?

So most of the time… I didn’t. I told myself the silence meant something about me.

Everything changed once I became the “busy” person on the other side.

I loved being helpful, so I started having back-to-back calls.

 • Offering intros.
 • Promising reviews.
 • Making mental notes.

And then life happened.

Deadlines. Kids. Travel.

I forgot to follow up, this time from the other side.

My lack of action wasn’t because I didn’t care but because startups (and life) are all-consuming.

Every now and then, someone would politely follow up.

And instead of being annoyed... I loved it!

I'd take the necessary action then and there and fire a message back to the person.

That’s when it clicked.

So many people sabotage their job search because they create these elaborate stories in their head to explain the silence.

The truth is almost always, "Oops, I got super busy and forgot. Thanks for reminding me. I'll fire that off right away."

Follow up isn’t about being pushy or loud. It’s about not taking silence personally.

It’s about understanding that “no response” usually means “not right now,” not “not you.”

Some of the biggest breaks in my career came from messages I almost didn’t send.

So if you’re trying to land your next startup role, remember this:

 • Following up isn’t rude.
 • Persistence isn’t annoying.
 • Being organized is a signal of seriousness.

The people who make it aren’t the ones who never hear “no.” 

They're the ones who don't vanish just because they didn't hear back.

𝗔 𝘀𝗶𝗺𝗽𝗹𝗲 𝗿𝘂𝗹𝗲 𝗜 𝘂𝘀𝗲 𝗻𝗼𝘄 𝗳𝗼𝗿 𝘆𝗼𝘂 𝘁𝗼 𝘀𝘁𝗲𝗮𝗹: If someone offered to help and hasn't responded in 5-7 business days, I follow up once via our last method of communication (email, LinkedIn, text). I'm polite, clear, and non-apologetic. I'll do this two more times and if I don't get a response after the three messages I move on.

The moral of the story is this...

Follow up. Ask again. Stay politely persistent. 

And don't take silence personally.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 for the next time you’re debating whether to send that message.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies.

Everyone wants Olympic-level results. Most train like it’s a weekend jog.

From the outside, the people who land incredible roles look effortless.

“𝘙𝘪𝘨𝘩𝘵 𝘱𝘭𝘢𝘤𝘦, 𝘳𝘪𝘨𝘩𝘵 𝘵𝘪𝘮𝘦.”

“𝘔𝘶𝘴𝘵’𝘷𝘦 𝘩𝘢𝘥 𝘤𝘰𝘯𝘯𝘦𝘤𝘵𝘪𝘰𝘯𝘴.”

“𝘗𝘳𝘰𝘣𝘢𝘣𝘭𝘺 𝘫𝘶𝘴𝘵 𝘨𝘰𝘵 𝘭𝘶𝘤𝘬𝘺.”

But here’s what you don’t see:

The hours of preparation.

The rejections.

The setbacks.

The learnings.

The adjustments.

The quiet consistency.

When I tell my story of joining early-stage Uber, I usually give the highlight reel:

 • Quit my job in Seattle
 • Moved to New York with no network
 • Had 90 days of savings
 • Landed a role at Uber just before money ran out

But the real story looked a lot more like Olympic training:

 • Waking up at 6 am to job search (treating it like a job)
 • Getting no response from message after message
 • Long stretches where it felt like nothing moved
 • Trying to figure out the value I could provide
 • No applause, no certainty, no shortcuts
 • Dozens of awkward networking calls
 • Rejection after rejection

The truth is, the job search is an endurance sport.

In the same way, Olympians don’t control the medal; they only control their training.

You don’t get to control the output; you only control your inputs:

Your clarity, prep, networking and consistency.

And just like elite athletes, most of the progress happens long before anyone sees the result.

The people who win in this market aren’t necessarily the smartest or most connected. They’re the ones willing to put in the work when no one’s watching.

Stop chasing the podium moment and start building the systems that get you there.

If you want to land a role that changes your career, ask yourself honestly:

Are you training like an Olympian… or jogging like it’s Sunday?

What stage of your job search are you in? Comment below with a single emoji:

📖 Learning
💼 Networking
🎯 Applying
🏆 Interviewing

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

I’ve helped 100+ job-seekers land roles in startups.
These are the 8 steps every successful search has in common.

You may think, “Those people are lucky.”
Right place, right time. Right connection, right company.

But after coaching hundreds of candidates, the pattern is painfully clear:
People who land great roles don’t rely on luck. 
They create luck their own luck by following a clear system.

A system that gets them unstuck when momentum dips, keeps them focused when the market feels chaotic, and helps them stand out when everyone else blends together.

Here are the 8 steps I see in every single successful search:
1. They get their mind right.

The job search is a sales process.

And in sales, there’s lots of rejection.

You have to steel yourself for the rejection to come. 

They create a plan for what it takes to get themselves into a peak state as often as humanly possible.

2. They get clarity before applying.

They define the exact role they want, why they want it, and what makes them a fit. 

“I’m open to anything” won’t cut it.

Clarity turns a chaotic search into a targeted one.

It makes every following step in the process easier and more effective.

3. They build a target company list.

Not 300 random companies, but 20-40 that match their skills, interests, and stage preferences.

This creates direction and eliminates distraction.

Batching this company/role searching also prevents random action.

4. Their LinkedIn and résumé signal credibility immediately.

They treat their LinkedIn/resume like a sales landing page crafted to stand out.

They make it clear to the reader who they are, what they do, the results they drive, and who they drive them for.

Every line is crafted to make hiring managers think: “I want to talk to this person.”

5. They track their progress

Applications, networking messages, calls, interviews, the works.

They understand what actions they’re taking.

The numbers tell them what’s working and what’s not working, and they adjust accordingly.

6. They send intentional outreach consistently.

Not mass messages.

No copy-paste templates.

Not “ChatGPT, what message should I send this person?”

High-quality messages that create genuine connection.

This is where most opportunities come from.

7. They prepare like a top candidate.

They run mock interviews, identify interviewer doubts, rehearse their stories, and study the company’s product deeply.

Most interviews are won in the prep.

8. They follow up and show real ownership.

Case studies. Value deliverables. Thoughtful notes.

They do the “free work” to show they’re operating like part of the team.

This is where offers are secured.

When you follow these steps, everything changes:

Your search stops feeling like hope.
Your outreach stops feeling random.
Your interviews stop feeling unpredictable.
And opportunities start showing up faster than you expect.

This will look like magic to those on the outside.
But you’ll know it’s a system.
And anyone can run it.

I've Helped 100+ People Land Start Up Roles

If it feels messy, you’re not doing it wrong. 

The job search is often the first real taste of start-up life. 

People think the chaos starts 𝘢𝘧𝘵𝘦𝘳 you land the role, but the interview process is just a warm-up. 

You’ll get ghosted. You’ll get rejected for reasons that don’t make sense.

A role you were excited about disappears overnight because priorities changed.

A hiring manager goes quiet because they’re juggling ten fires at once.

It’s frustrating and knocks your confidence. And it can make you start questioning yourself.

But it’s not personal, and it’s not a reflection of your ability.

It’s just how startups operate.

They move fast. They change direction. They make decisions with imperfect information.

And once you’re inside a startup, that doesn’t suddenly stop.

 • Priorities shift week to week.
 • Teams are small, so your impact (+ your mistakes) are visible.
 • Everything is an experiment.
 • You’re constantly adjusting in real time.

That’s also why the people who love startups 𝘳𝘦𝘢𝘭𝘭𝘺 love them.

They’re comfortable with ambiguity. They enjoy figuring things out as they go.

They don’t need everything to be perfectly defined to move forward.

So if you’re in the thick of the job search right now, feeling behind, dealing with setbacks, wondering if you’re doing something wrong… pause for a moment.

 Think of this process not as a punishment but as preparation.

You’re learning how to stay steady when things feel uncertain.

How to stay energized and excited while working hard.

How to keep showing up when plans change.

How to continuously experiment, measure results, and iterate. How to stay energized and excited while working hard.

How to separate noise from signal.

And guess what?

That’s exactly what you’ll need on the inside.

So keep going.

Even if “going” today just means sending one message.

Just take that first next step in the right direction.

The people who make it through the search are usually the ones built for the work.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

How long has your startup job search taken so far?

There’s no “normal” timeline - everyone’s path looks different.

But understanding the range helps you see you’re not behind… you’re human.

How long has your startup job search taken so far?

What does it actually take to break into an AI startup as a TPM?

In this case: 287 cold messages, 1 strategy, and 3 frameworks anyone can copy.

This is Amr’s story, and it’s a perfect example of what happens when someone stops treating a job search like guesswork and starts approaching it like a system.

Five months ago, Amr joined Early with one clear goal: get a Technical Program Manager role.

Not “see what comes up” or “apply generally.” He chose the role deliberately, built toward it, and committed to doing the work most people avoid.

Along the way, he used three frameworks that completely changed his results - and anyone reading this can copy them.

1. Treat outreach like a game and track your numbers.

Most people rely on feelings when they job search. 

“It feels like no one is replying.” 

“It feels like my messages aren’t working.”

Feelings are unreliable. Data isn’t.

Amr sent 287 cold messages. His response rate was 14%. His call rate was 26%.

By tracking the numbers, he could see exactly what was working, which messages landed, and where to double down.

The lesson: you can’t improve what you don’t measure. Treat it like a continuous game.

2. Personalize your outreach using your real interests.

Personalization isn’t forced flattery or dropping someone’s name into a template. It’s creating a REAL human connection.

Earlier in the year Amr visited the Rocky Mountains for the first time and absolutely loved it.

Whenever he reached out to someone based in Colorado, he mentioned that trip.

This wasn't some sort of trick or tactic. He genuinely wanted to share how much he loved the area. 

Guess what? 

That human touch dramatically increased replies.

Most people send messages that read like AI wrote them. Amr made sure he sounded like a real person.

3. Reach out to multiple people at the same company.

This is the most uncomfortable step, but also the most effective.

For the TPM role, Amr didn’t message one person - he messaged nine.

Four replied. Three had conversations with him. One referred him internally.

When you rely on a single point of contact, your chances are low.

When you create multiple internal touchpoints, you drastically increase your referral chances.

This is how applications get resurrected, moved forward, or re-reviewed even after initial rejection.

Amr didn’t get lucky. He built a repeatable system that made success inevitable.

TL;DR: Track your outreach so you know what’s actually happening. Personalize your messages so people want to reply.

Send multiple messages to people at the companies so you’re not depending on one person’s kindness.

You don’t need dozens of people to say yes, you need one. And these three frameworks dramatically increase your odds of getting it.

📌 Save this post - you’ll want it when your next interview loop starts.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

In 2026, being qualified isn’t enough.

Hundreds of qualified applications are being submitted for every role even at startups most people have never heard of.

I was speaking with a VC Head of Talent and she said several of their portfolio companies (we’re talking tiny, early-stage, low-visibility startups) now get hundreds of applicants per role.

Not because the roles are special, and not because the comp is outrageous.

But because the volume of people applying has exploded and the use of AI tools and bots has made it even worse.

Being qualified gets you into the pile, but it won’t get you into the room.

Only visibility can do that.

I saw this again with a candidate I coached. 

Brilliant background. 
Great skills. 
Perfect match on paper.

He’d applied to ~60 roles with almost no traction.

Except one.

For that one role, he reached out directly.

He wrote a personal note, sent it to the founder, a recruiter, and a few people on the team. 
He showed them why he cared.
He made himself visible.

And instantly, he moved forward.

Here’s why visibility wins:

𝟭. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗳𝗼𝗿𝗰𝗲𝘀 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁𝗶𝗮𝘁𝗶𝗼𝗻.

Everyone is qualified, but very few take the time to write personal messages, share context, or reach out to internal stakeholders.

When you do, you’re no longer competing with the full pile. 

You’re competing with the handful who bothered to do a little bit more work.

𝟮. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝘀𝗶𝗴𝗻𝗮𝗹𝘀 𝗶𝗻𝘁𝗲𝗻𝘁.

If you send a thoughtful note to the hiring manager, you’re no longer “one of 300 applicants.”

You’re a real human who cares about their mission and what they’re building and wants to help.

Founders, recruiters and teams notice it.

Trust me, I have the receipts. 

Dozens of messages from recruiters and hiring managers saying, “Wow, this is a really unique way you reached out. It really made you stand out.”

𝟯. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗼𝗽𝗲𝗻𝘀 𝗱𝗼𝗼𝗿𝘀 𝘁𝗵𝗮𝘁 𝗿𝗲𝘀𝘂𝗺𝗲𝘀 𝗰𝗮𝗻’𝘁.

Referrals.
Internal conversations.
Warm intros.

The thing that moves you forward is you making yourself known to the people who matter.

So in 2026, the question isn’t:

“Am I qualified?”

It’s:

“Have I made myself visible to the people making the hiring decision?”

If not, the most talented version of you will stay buried under 300 other clicks on “Apply.”

The candidates who win this year will be the ones willing to reach out, write personal notes, send value, and make themselves impossible to ignore.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you

You think you’re being judged on your answers.

Founders are actually judging your signals.

Interviews, especially in startups, aren’t exams, they’re calibration exercises.

Most candidates show up obsessing over “saying the right thing.”

Meanwhile, founders are watching for something completely different:
Your signals.

And if you learn how to control the signals you send, your interviews instantly feel easier, clearer, and more predictable.

Here are 5 signals founders are judging, and how to nail each one:

1. How you react to friction.

There is no "standard startup interview process".

Hiring in startups can be messy, so expect more friction than a normal interview process.

More rounds. Trial tasks. Follow-ups. Unclear next steps.

If you expect this level of friction instead of being surprised by it, you stay composed while everyone else spirals.

Signal: resilience, realism, emotional steadiness.

2. Prepare like an interviewer

Founders want someone who understands and is excited about the product, the market, and - ideally - them.

Research the company like you’re the one hiring.

It may sound crazy, but people who share excitement about their product and the team are rare.

Signal: high-agency thinking, ownership, genuine interest.

3. Confidently show your strengths

Interview answers matter, but founders are tuning into:

– How you think
– What results you’ve produced
– What problems you can take off their plate

Be able to not only share what you've done, but how that experience tracks directly to what they need.

Signal: clarity, competence, self-awareness.

4. Understand that roles evolve

It is not abnormal for the original job description to change.

Funding, market dynamics, team changes, and strong candidates change quickly and can change what the company needs.

If you can articulate what additional value you bring, you’ll stand out instantly.

Signal: adaptability, initiative, strategic thinking.

5. Fix your mindset

The best interviewers aren’t rigid.

They’re calm, flexible, curious, and collaborative.

Going in with “I hope they like me” energy kills your performance.

Signal: confidence without ego.

The more you master these signals, the easier interviews become - not because you’ve memorized better answers, but because you’re playing the same game the founder is.

As someone who’s been on the hiring side:

Founders aren’t looking for perfection, they’re looking for patterns.

Do you think clearly?

Can you handle ambiguity?

Will you take ownership without needing permission?

Do you bring something the team doesn’t currently have?

Can you grow as fast as the company grows?

These signals tell founders far more than any polished answer ever will, and once you understand that, interviews become less about performing…

and more about demonstrating how you operate.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

Some of the biggest opportunities of my career came from a message I almost didn’t send.

You’ve likely been there.

Message typed out. Cursor hovering over the send button. Mind racing. Questioning every letter and punctuation.

Overthinking something you 𝘬𝘯𝘰𝘸 will be needle-moving for your career. 

Worrying about timing. Tone. Whether it’s worth following up at all. 

But thick skin is a requirement in the startup industry. 

There are a few things you have to get comfortable with if you want to break into or continue to work in startups.

1️⃣ 𝗙𝗶𝗿𝘀𝘁, 𝗯𝗲𝗶𝗻𝗴 𝗶𝗴𝗻𝗼𝗿𝗲𝗱.

I used to think silence meant I didn’t catch their attention. 
Now I know it usually means the other person is drowning in work. 
Startups run on chaos. 
People forget. 
Priorities shift hourly. 
A follow-up isn’t rude. On the contrary, it’s helpful.

2️⃣ 𝗦𝗲𝗰𝗼𝗻𝗱, 𝗿𝗲𝗷𝗲𝗰𝘁𝗶𝗼𝗻 𝗮𝗻𝗱 𝗳𝗮𝗶𝗹𝘂𝗿𝗲.

I used to replay every “no” in my head.
What did I say wrong? 
Did they not like me?
What should I have done differently?
But after hiring hundreds of people myself, I’ve learned that rejections are rarely personal.
Sometimes the budget changes. Sometimes the role changes. Sometimes the founder meets someone who’s been doing the exact job for 10 years. 
Rejection and failure always teach you something.

3️⃣ 𝗧𝗵𝗶𝗿𝗱, 𝘁𝗵𝗲 𝗳𝗲𝗮𝗿 𝗼𝗳 𝗯𝗲𝗶𝗻𝗴 𝗮𝗻𝗻𝗼𝘆𝗶𝗻𝗴.

This one took the longest to outgrow.
I didn’t want to bother anyone.
Didn’t want to seem pushy, or follow up “too soon.”
But in reality, busy people appreciate persistence.

It shows you’re organized, committed, and serious.

I can’t count the times someone followed up with me, and I replied, “Thank you! I completely forgot about this.”

If you want to work in startups, you can’t let sensitivity stop you from showing up.

Thick skin isn’t about being loud or abrasive.

It’s about staying in the game long enough for the right opportunity to find you.

Follow up.
Ask again.
Try again.
Apply again.

Because the people who land the great startup roles aren’t the ones who never hear “no.”

They’re the ones who don’t let “no” stop them.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

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