Tobi Oluwole

Founder & CEO, Magnate Ventures, Founder’s Blueprint Accelerator | Growth Advisor, Speaker & Investor

With over 330M+ impressions, & 375,000 LinkedIn followers and over $35M in revenue generated for clients, I created a blueprint that drives leads, closes sales, and creates freedom for entrepreneurs. 

In 2019: I was working in tech sales struggling to hit my quota
In 2020: I started creating LinkedIn content, testing what works.
In 2024: I’m helping founders, leaders, and entrepreneurs grow their audiences and businesses by turning their thoughts into LinkedIn content that turns followers into customers. 

I’ve coached and worked with 100+ founders & entrepreneurs helping them craft stories, grow their following, and build profitable lifestyle businesses—all using the data that helped me make my first $1 million using LinkedIn.

Here’s how I can help you:

1. Subscribe to my newsletter - tobioluwole.com

2. Check out my free webinar on how to build high-ticket offers: https://www.tobioluwole.com/replay-signup-page

3. Apply to the next cohort of my 8-week accelerator, The Founder's Blueprint: https://foundersblueprint.ai 

Not ready yet? No problem. Stick around! I share actionable tips on entrepreneurship, leadership, & personal growth

100,000+ people are waiting for you to tell your story. 

Start writing on LinkedIn today.

📩 For sponsorships or partnerships: tobi@tobioluwole.com

Founder

Founder & Coach providing actionable advice on how to earn more and live happier.

I'll never forget the first real mentor I had.

He referred me for a role that I had no idea about.

Every chance he got, he would nominate me for opportunities.

So as soon as I became I lead, I took the same approach.

Because that's what great leaders do:

Try to get you into rooms you don't know exist.

Founder @ Magnate Ventures & The Founder’s Blueprint | Angel Investor & Speaker

I came to Canada against my will in 2010. 

My dad wanted me to continue my education here but I wanted to study in the UK. 

For the first week, I was resentful then I slowly fell in love with the country.

But things were not always smooth. 

There was a year when I crashed on friends' couches because I didn't have a place to stay. 

Most of my side hustles were started because I absolutely needed the money to live! 

But in 2020, I landed a role at Shopify on my 7th attempt and that was the start of my new life. 

2 months later, my wife and I bought a pre-construction house. 

1 year after that we moved into our new home. 

In 2022, I became a Canadian Citizen.

Then in 2023, we sold our first home and bought this second one that will be our family home. 

My businesses was making more monthly than I used to make annually in my first job when I left corporate.

Today, I get to take care of my family and travel the world with my wife. 

There were so many moments when I felt like I wanted to move back to Nigeria.

And many days when I thought entrepreneurship would never work for me.

But I'm glad I didn't. 

Never give up on your dreams.

Last year, Mark Zuckerberg just paid someone $1.5 BILLION to join Meta.

Then Meta announced that they're laying off 600 people. 

The person Mark hired is Andrew Tulloch, Co-Founders of Thinking Machines Lab. 

Andrew's startup is already worth $12 billion even though they haven't released a product yet. 

And the 600 people getting laid off will receive 16 weeks severance. 

There's a something so unbelievable about this whole story. 

But it just reinforces what I've always believed: 

Companies will always do what is best for them first. 

So it's your responsibility to do what is best for you too. 

Build something you own.

I recently met a young lady who: 

→ Quit her job at 23
→ Bought a traditional business 
→ Grew it to over $1 million in revenue

All before she turned 25. 

Now she spends her days working for herself, spending time with her family and travelling more often. 

I can't imagine what the next 30 years will look like for her. 

You can't add days to your life. 

But you can add life to your days.

I fired one of the best employees I've ever had. 

Because I figured out how great of an entrepreneur he actually was. 

I got a cold message from Tosin Togbe on LinkedIn back in 2022. 

He was living in Nigeria but looking to land roles with companies in North America. 

We stayed connected and in 2024, I decided to hire him into our sales team. 

This guy learned insanely quick & crushed it in sales which wasn't surprising! 

But what was even more incredible was how much he was learning behind the scenes in his own time. 

I was paying him pretty well but I realized that I was holding him back. 

So I gave him a big bonus, fired him and told him to build his business. 

We stayed close friends and kept chatting every month. 

My theory was that he could likely out earn whatever we could pay him.

→ He studied all my LinkedIn frameworks and now has 15,000+ followers
→ Learned how to productize his knowledge & build high-ticket offers
→ Learned how to negotiate brand deals now makes 4-figures/month
→ Learned how to delegate and hired his brother to run his brand

Last month, I got to meet Tosin for the first time while I was in Lagos & he gave me an update.

→ He got married & gets to travel almost monthly with his wife
→ His solo business generating 9x what I was paying him
→ He's building a home for his parents in Nigeria
→ Bought land & built his own home too 

What a journey! 

Proud of you Tosin Togbe!

It's insane how quickly entrepreneurship can change your life.

I spent the last 6 days in Dubai at the 1 Billion Followers Summit

And I can't believe what I just experienced. 

30,000+ attendees, 400+ Speakers and so many unbelievable lessons.

As I gave the closing keynote on one of the stages, all I could think was: 

I can't believe how much posting daily on LinkedIn alone has changed my life.

And the quality of relationships that it has produced. 

If you're on the fence about doing something big in 2026... 

I encourage you to just start with something small and keep going for the next 3-5 years. 

It just might change your life.

My incredible business track-record

1st business: Failed
2nd business: Failed
3rd business: Failed 
4th business: Failed
5th business: Failed 
6th business: Failed
7th business: Failed
8th business: Failed
9th business: Failed
10th business: $500k
11th business: $3 million
12 business: Launching

You can’t lose if you don’t quit

Before I became a tech sales rep, I had no idea that job existed. 

Before I joined Shopify as a Customer Success Manager, I had never heard of that job title. 

Before I started my career bootcamp in 2019, I only had 4 years of work experience. 

We helped 30 people land jobs & I had never even worked in recruiting. 

Before I went viral on LinkedIn in 2020, I didn’t know “content creation” was a thing. 

Now I run a 7-figure company that’s powered by LinkedIn. 

And our systems have helped founders generate over $21M in revenue in the last 3 years. 

Stop telling yourself that you need to be qualified enough to do things. 

Growth comes from doing things you are not qualified to do yet.

My COO, Callie, is one of the greatest blessings that I got as a Founder. 

She loves everything I hate about building my business. 

And because of her, we've been able to double our business every year. 

All my founder friends ask me every year how I found her.

And how I knew she would be an amazing co-founder.

There were 9 specific things Callie did (and still does) that made her perfect for this role. 

1. She translates rough ideas into clear systems. 

2. She executes first then asks questions second. 

3. She has very high integrity in every single area of her life. 

4. She went from being a waitress to becoming a CPO at a startup.

5. She believes that what's best for the business is the best decision. 

6. She constantly realigns me and the company with our core values.

7. She's always looking for solutions to problems I haven't even found yet. 

8. She gets more done in 4 hours than most people can do in 3 or 4 full days. 

9. In her free time, she's always taking some course or learning something new.

Six months into working together, she officially became my Co-Founder.

Today, she's also one of my closest friends. 

Your ability to attract people smarter than you is key to building a great business. 

When you find these people, take really good care of them.

My LinkedIn impressions after 6 years of posting: 

Year 1: 4 million views
Year 2: 11 million views
Year 3: 79 million views
Year 4: 52 million views
Year 5: 136 million views
Year 6: 49 million views

330 million eyes have seen my content 

Just because I posted it. 

Stop overthinking. 

Just make the first post. 

Consistency always compounds.

Last year, I spoke to a guy who quit his $130k job to be an entrepreneur. 

I told him this was a terrible idea. 

He said he had found a business online that would make him rich. 

The truth is that he was probably right. 

But the problem was that he had never even tried to run a business before. 

So he spent a few months "working on the branding". 

And then hired someone to "help shape the go-to-market strategy."

6 months later, we caught up for coffee and I asked: 

"How many potential customers have you spoken to?"

He said, "Oh we're not ready to launch yet so none."

At that point, I knew this idea wasn't going to make it off his laptop. 

And it never did. 

He ran out of money, and his wife made him get another job. 

I've seen this so many times. 

You don't have to quit your full-time job to start building your own business. 

Use your evenings and weekends, post content online and find a problem people want help solving. 

"Go big or go home" is how so many people end up back at home. 

Start small and move quick.

"Networking" is highly overrated. 

Genuine friendships are greatly underrated. 

If you go into every conversation trying to get something out of it

You end up missing the entire point of what life is about. 

→ Creating memories with people
→ Growing and developing together
→ Being able to let your guard down
→ Sharing good and bad days as they come. 

Relationships are what make life so worthwhile. 

Transactions, deals & business born out of those relationships last longer.

A founder I worked with for 8 weeks just hired a wealth manager. 

Before we worked together, his side hustle made less than $25k in a year. 

In November 2025, that same business earned $90,000 in one month. 

So this founder did what I wish I did years ago. 

They hired someone to manage their money. 

The biggest mistake I see from entrepreneurs is that they try to figure everything out on their own. 

→ How to build better offers
→ How to hire the right people 
→ How to scale with paid marketing
→ How to manage their money as it grows

I made this mistake & lost a ton of time and money thinking I was smarter than I was. 

If you want to go to the next level in your business

Just hire people that have been to that level before.

Stanley (Your Content Coach) is giving away $100,000 USD! 

To cover your living expenses and rent for an entire year so you can go all in on your dream.

When I started creating I was terrified what people would think so I hesitated for 5 months! 

But I did it anyways and have been posting for over 1,600 days straight.

That decision changed my entire life. 

Then I was terrified to quit my job in 2023 to become a a full-time entrepreneur. 

Because I went from having a 6-figure tech salary to being fully responsible for myself!

Now my tiny side hustle has become a 7-figure company that allows me to live anywhere in the world with my wife. 

If your salary and rent were covered for a year, what would you create?

2026 is your opportunity to build a totally new life: 

Here's what you need to do to enter the Dare To Dream competition: 

1. Sign up for Stanley (free)
2. Post a video (2 mins or less) on your public Instagram or TikTok sharing your story, your dream, and how you plan to bring it to life using #standaretodream26 and tag Stan on LinkedIn
3. Complete the Typeform after signing up

All details here: : https://lnkd.in/grC5PP-p

You will never feel fully ready to do anything because "ready" is not an emotion.

What's your dream? 

#StanPartner #DareToDream

I spoke to a founder that "got lucky" last year. 

She spent 15 years working insanely hard as a recruiter.  

Then one day decided to just build her own recruiting company. 

In her first year, the business made $150k in revenue. 

One of her clients was so impressed with the quality of her candidates that he introduced her to a friend. 

That friends was the head of a startup that had raised over $100 million and was ready to expand quickly. 

She helped them hire hundreds of extremely talented people across the world. 

So in only her second year in business she hit $5 million in revenue. 

This year, they'll do over $15 million. 

I asked her what made her so successful and she started laughing. 

Then said "I guess I got lucky"

What people consider as luck is usually just years of hard work behind the scenes. 

The harder your work, the luckier you will get.

In 2019, I used to charge $150 for a resume review.

To me, that was a lot of money - not only to spend, but also to charge.

I sucked as an entrepreneur for many years no matter how hard I worked

It seemed like I just could never generate enough money to take care of myself & my family.

That's all I actually wanted - to be completely self sufficient. 

But I didn't know what I didn't know.

Eventually, I found the Hormozi videos. The Russell Brunson breakdowns. 

The endless "how to create an offer" content.

It didn't click right away.

But by 2021, I finally figured it out. 

So I broke down exactly what finally worked for me.

The 8 steps we now use (and teach) to build high-ticket offers that actually sell.

I recorded the entire framework in ​a 20-minute video​: https://lnkd.in/giP_gq3X

None of this is theory. 

The 8 P's:
→ Problem (and why you must start here)
→ Persona (who you solve it for matters more than what you solve)
→ Prototype (all the ways you could solve this)
→ Package (making it feel premium)
→ Positioning (your unique mechanism)
→ Pricing (why it must be high)
→ Payment plans (the structure most people mess up)
→ Promotion (where 90% of people fail)

Here's the truth: you can nail the first 7 steps and still struggle to make any money online.

Because step 8 is where you actually generate real revenue.

If you've been sitting on expertise but can't figure out how to turn it into revenue, this will change that.

Link is in the comments

My longest standing meeting has been running for 4 years. 

With Sefunmi Osinaike!

We both launched our career businesses around the same time. 

Our businesses have completely evolved but we still have a monthly meeting where we talk through our biggest challenges.

And also get to share our biggest wins when they happen. 

While I was living in Paris, Sefunmi flew in & came to lunch straight from the airport so we could have lunch together. 

He was on the verge of a massive life decision and it felt more appropriate to have the conversation in person. 

One of the best parts about being a builder is meeting people who are smarter than you AND who make you feel safe. 

Surround yourself with those people and you will win in the long-term.

One of the best things about living in Paris was meeting Ariel Renous

We met on LinkedIn and decided to go for lunch. 

On our second meeting he asked me to teach a class on Personal Branding for his company Augment.org

My first thought was "I'm not sure if he's being serious"

My second thought was "This guy must really believe in me"

Well I said "Yes" and a few weeks later, I spent 6 hours with the Augment team recording. 

That one project has led to:

→ New relationships with some awesome entrepreneurs
→ Millions of dollars in revenue for both our companies
→ Tons of credibility & countless opportunities for me 

But most importantly, an incredible friendship with one of the most generous humans I've ever met in Ariel. 

Every time we meet for lunch I leave with so many lessons and a ton of wisdom!

I'm 100% sure this guy is going to build a once in a generation company with Augment.org

And can't wait to witness it. 

Play long-term games with long-term people.

I am so glad I left my corporate job at 28 years old. 

Because entrepreneurship just isn't that risky anymore.

If you wanted to start a business 30 years ago, you would need:
→ $50,000+ in startup capital for inventory, office space, and equipment 
→ Physical storefronts with long-term lease commitments 
→ Business loans with your house as collateral 
→ Expensive advertising in newspapers, TV, or radio 
→ Employees from day one just to operate

Today, all you need is:
→ A little bit of courage
→ A laptop/phone and internet connection 
→ $0 to start (free social media, free tools) 

The barrier to entry has completely collapsed.

The real risk now isn't starting, it's staying stuck in a job that caps your potential while watching others build the life you want.

Stanley (Your Content Coach) gets this.

That's why they're removing the last excuse: money.

Their Dare To Dream campaign is going to change lives. 

One person will receive $100,000 to fund their entire 2026 

And 5 more people get $10,000 each

Everyone who enters also receives:
→ Lifetime Stan Pro Access 
→ Featured across Stan's marketing campaigns
→ Coaching from successful creators and entrepreneurs 

If you’ve been on the fence about building your own thing, this is your opportunity

1. Sign up for Stanley (free)
2. Post a video (under 2 minutes) on Instagram or TikTok sharing your story, dream, and plan using #standaretodream26 and tag Stan on LinkedIn
3. Complete the Typeform after signing up

Full details here: https://lnkd.in/grC5PP-p

What’s your dream?

#StanPartner #DareToDream

It took me 11 years of constant effort to make my first $50k online. 

Then another 3 full years of grinding (while working a full-time job) to make my first $1 million. 

Then in 2024, we hit a million in revenue in 12 months. 

They say your first million is the hardest to make. 

And it's very true. 

But here's what happens once you hit it: 

1. Your self-belief reaches a point of no return 

No matter how good or bad things get after this milestone you will always have one thought at the back of your head: 

"I did it once. I can do it again." 

Your ceiling becomes your new floor. 

2. You realize how often you are wrong

The best athletes in the world miss 70% or more of their shots. 

The same applies to entrepreneurs. 

Sometimes your best ideas won't even come from your brain and you learn to accept that. 

3. You want to share everything you're learning

At least this was true for me. Because of how long it took me to figure it out. 

My goal automatically shifted to helping great entrepreneurs figure it out in less time than it took me. 

It gave me more fulfillment than I ever imagined. 

Next week, I'm hosting a private workshop next Tuesday for 100 founders. 

To pull back the curtain on what it actually took to scale our business. 

Reserve one of the seats here: https://lnkd.in/g3BS6wGr

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!

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.

taplio

The Battle

Tobi Oluwole

Kyle Thomas

Followers

Posts

Engagements

Likes

Performance ScoreTobi Oluwole's LinkedIn Performance

Performance ScoreKyle Thomas's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Tobi Oluwole

Kyle Thomas

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Tobi Oluwole's LinkedIn Performance

Performance ScoreKyle Thomas's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreTobi Oluwole's LinkedIn Performance