Top 10 Lessons From 2023's Most Successful Startup Job Seekers

JOB SEARCH STRATEGY
Copy The Best Job Hunters of 2023.

In June of 2022, Avo, the same-day grocery delivery startup where I worked made a hard pivot, closed operations, and laid off the entire team.

Since then, I have leaned into helping others live their dream startup careers via the Early Accelerator.

2023 was my first full year with my new focus, and we saw amazing results.

The average job search was only 2.4 months - ½ of the US average.

We increased total compensation by over $1,000,000.

The average person got a salary increase of over $24,000 (a additional crispy $2k in the wallet each month) and equity increases of over $100,000 (I’m hopeful some of these will turn into millions).

As I reviewed the job seekers who saw the fastest success in the last year, 10 common traits stood out.

Today, we’ll not only identify these traits but also enrich them with real-life stories, expert opinions, and actionable advice to help you on your journey to startup success.

Whether you’re actively job hunting or just curious about the startup world, there’s something here for everyone.

PAY-IN-FULL
They Invested In Themselves.

Investing in yourself goes beyond the financial commitment.

It’s about a mindset shift.

All people who landed jobs in less than three months (with just one exception) paid for the Early Accelerator in full vs making payments.

Those who joined weren’t just buying coaching and a community.

They were making a clear statement of their commitment to personal and professional growth.

You don’t need to invest in my program, but figure out a way to make a commitment to yourself you can’t go back on.

For many, investing money in a coaching program, a community, or a course is the easiest way to do this.

But there are also effective non-monetary solutions like investing your time and making public commitments.

👨 Real Life Example: Lauren was laid off from her job as Director of Operations at a child ed-tech company. She had a little one at home and wasn’t sure about making the financial investment, but knew it was a way to keep herself accountable and get expert guidance. It may sound crazy, but the day she joined the program, she received outreach from a company looking to hire her for a Program Manager position. She landed the position the day of our first live session and said her investment was 100% worth it. It’s all a matter of perspective.

🧠 Expert Insight: Dr. Helena Richardson, a career development psychologist, explains, "Investing in oneself can take many forms. It's the act of prioritizing your growth that truly matters. Whether it's through time, money, or public commitment, the key is to set a goal that is meaningful and challenging enough to propel you out of your comfort zone. This commitment leads to a transformative journey, both personally and professionally."

⏩ Actionable Step: Start by identifying what kind of investment resonates most with you. If financial investment isn't feasible, consider dedicating a set number of hours each week to job-hunting skill development or setting up a public goal on social media or with your personal network. The most crucial part is to make this commitment concrete, be it through a written plan, a public declaration, or a scheduled routine. Stick to this plan, and remember, the commitment you make today is an investment in your future success.

GIVE-GIVE-GIVE
They Competed on Generosity.

Generosity in the job market is a game-changer.

These candidates never shied away from going the extra mile, offering valuable contributions without immediate expectations in return.

They understood that people pay for implementation, not information.

They gave it all away so people would say, “If that’s how much value they deliver outside the company, imagine how much they’ll be able to deliver once they’re actually inside.”

👨 Real Life Example: Stephen sent value at every touchpoint in his interviews with a target company. He recommended movie theaters and pizza places in NYC. He shared screenshots of ways he had helped build culture at his previous company. He sent one-pagers to help the company with its business development. He drafted up considerations for the company based on upcoming regulations for transportation in their primary market. Low and behold, he stood out from all the other candidates and landed the job.

🧠 Expert Insight: “Relationships are leverage. If you give value to someone else first, you have leverage.” - Gary Vaynerchuk

⏩ Actionable Step: Look at all your work in your career. Is there something you’re so good at you can rattle off how to do it by memory? Take that subject and write a playbook. Share that playbook on your LinkedIn and any relevant person you connect with. Ask questions about problems at the company relating to your area of expertise and once you’ve uncovered areas you can help, send connections, resources, information, playbooks, spreadsheets, or case studies. Anything that will show you thought of them and went out of your way to find a solution.

DON’T BE AFRAID TO ASK
They Asked For Help

Often, I speak with job seekers in month 3 of their job search.

What held them back from reaching out at the start of their job search?

They weren’t willing to ask for help.

The job seekers who landed the jobs the fastest sought feedback, asked questions, and looked forward to learning opportunities.

They saw failures as a way to improve and accelerate, not a setback.

If they didn’t understand something or wanted to know best practices, they didn’t guess, they asked.

They asked me, fellow job seekers, experts in their industry.

They sought out the best knowledge they could gather from the people who had lived it before.

👨 Real Life Example: Matt participated in more mock interviews than anyone in the program’s history. He shared the role he was interviewing for, the interviewers’ profiles, the background on the process so far, and the areas he was most interested in improving. He wasn’t afraid to get feedback publicly and put himself into the mock-interview hotseat. As a result, he landed a job in less than 2 months.

🧠 Expert Insight: “Now, I’ve actually found something to be very true, which is most people don’t get those experiences because they never ask. I’ve never found anybody who didn’t want to help me when I’ve asked them for help.” - Steve Jobs

⏩ Actionable Step: Don't hesitate to ask questions, whether in professional networks, forums, or during informational interviews. Engage with your community. Google “Free [INSERT YOUR FUNCTION OR INDUSTRY HERE] Community”. You’ll be able to find a large group of people who are familiar with your industry or function to ask questions of. Also, don’t shy away from reaching out to people one or two steps ahead of you and asking them how they did it.

STAND OUT
They Put Themselves Out There

Do what everyone else is doing (submit application, reach out to recruiter, wait) and you’ll look just like everyone else.

Stand out and you’ll become a candidate of one.

But, standing out often means stepping out of your comfort zone.

These job seekers embraced vulnerability to showcase their unique skills and personality.

They recorded videos of themselves and sent them to leaders at target companies.

They reached out to investors, executives, and others they felt might be “out of their league.”

They did everything it took to stand out from the pack despite how much discomfort it caused.

👨 Real Life Example: Sarah was always on the hunt for new tools to allow her to stand out from the crowd. She used ChatGPT prompts, cover letter AI tools, and found a useful video recommendation tool called allUP. After using allUp in her job search, she learned they were hiring stood out through her willingness to record herself and share those recordings with the company as a part of the interview process. She landed her role at allUp in just 2.5 months.

🧠 Expert Insight: Charlie Hoehn got his first job out of college by sending a cold email to a best-selling-author, Caleb Ralston landed his job working with Gary Vee by sending him a video, Ryan Graves became Uber’s first CEO by sending a tweet to the founder. They all did what was necessary to stand out from the pack and highlight their interest and hunger.

⏩ Actionable Step: When you feel discomfort, lean into it. Discomfort is growth in disguise. Remember that most people don’t get out of their comfort zone and as a result, they don’t stand out. So record a video introduction with highlights about why you want to speak with a key member of the team at a target company and send it to them. Send that connection request, email, or DM that has your heart pounding. Do what makes you uncomfortable because odds are it makes others uncomfortable too and they’re avoiding it and blending in as a result.

RAPID APPLICATION
They Took Quick Action & Adjusted

Adaptability and responsiveness were key.

Learning something new was immediately followed by the application of the learning and adjustment based on feedback.

They were taking massive and rapid action.

👨 Real Life Example: Michael interviewed for a Sales Director position that sounded great, but after getting deep into the interview process, he identified some serious red flags. He withdrew himself from the interview process, crafted questions to uncover those red flags in other existing interview processes, implemented them immediately, and landed a job as Director of Global Sales.

🧠 Expert Insight: “Without knowledge action is useless and knowledge without action is futile”- Abu Bakr

⏩ Actionable Step: Perform a post mortem after every major action you take. For example, after an interview, after sending 10 cold outreach messages, after crafting a value deliverable and sending it to a connection. What went well? What didn’t go well? What can you change in your approach to improve the results? Make those changes and try again as soon as possible.

ETERNAL OPTIMISTS
They Remained Optimistic

Maintaining a positive outlook, despite challenges, was another common trait.

Even though they had short job searches, every single one of them saw many rejections.

Outreach that went ignored.

Interviews that resulted in rejection.

However, they saw each rejection as a step closer to the right opportunity.

They knew it was all in service of a better tomorrow on the other side.

👨 Real Life Example: Kevin was making the move from VP to COO and had an interview with one CEO/Founder who was outright rude, condescending, and had him questioning his abilities. But, not to be deterred, he knew his desired outcome and what it meant for his future and believed in his ability to get there. In a few weeks after the initial rejection, he landed his dream COO role.

🧠 Expert Insight: “I come from Silicon Valley- and in Silicon Valley, the cynics get to be right and the optimists get to be rich.” Shaan Puri.

⏩ Actionable Step: To stay optimistic I like to keep my highlight reel closeby at all times. What does this mean? Look back at all your prior roles and list out the projects your most proud of and the projects that delivered the most significant results. Put those on a list and keep that list visible for you to see all the badass results you have driven. When you’re doubting yourself, just review the list.

WHAT’S YOUR WHY?
They Had A Clear “Why”

A strong, personal "why" drove these individuals.

This deep motivation was often rooted in personal values or aspirations.

Some were doing it for their children.

Some were doing it for their children who were yet to be born.

Some were doing it to save the planet.

Some were doing it to escape a bad situation.

Others were doing it to get exposure to the work they wanted to do for the rest of their lives.

Each one was different.

But everyone had a “Why”.

👨 Real Life Example: Colby was working a great company before layoffs, leadership departures, and a role change completely altered his experience at work. He had a baby on the way in a matter of months and knew he wanted to be in a new work home for at least a few months before taking paternity leave. Talk about a strong “why”! He took massive action and landed a job in less than 1.5 months.

🧠 Expert Insight: “When we know WHY we do what we do, everything falls into place. When we don’t, we have to push things into place.” - Simon Sinek

⏩ Actionable Step: Write down your goals, your hopes, your dreams. Then write down why you want each of those things. You’ll find that writing the thing is far easier then writing why you want that thing. Go back to that why everytime things get difficult. The compelling “Why” you have created justifies the work you’re putting in.

FIT OVER FINANCES
It Wasn’t All About The Money

If someone comes to me and says, “I want to job that will pay me the most money in the least amount of time possible. Can you help me?”

My answer is no.

I’m not primarily about money because I know that if I pursue areas where I have a competitive advantage and where I’m interested I’ll do my best work and will be paid well.

That’s true for each of the most successful job seekers of 2023.

They prioritized fit and passion over salary.

Their focus was on finding roles where they could make a real impact and that would accelerate their careers toward their ideal version of the future.

Leaning into roles and companies that interested them allowed them to go above and beyond in the outreach, interview preparation, and value creation leading them to rapid success.

👨 Real Life Example: Pritesh had a great career at Uber and as a startup VP but wanted to make the C-Suite jump. For him, money was important but more important than increasing his compensation was his ability to get the skills, experience, network, and teachers that came from being the COO of an early-stage startup. With that focus, he landed an early-stage COO role and didn’t have to take a step back from his previous salary.

🧠 Expert Insight: “At best, undervaluing experience slows career growth, actually leading to lower lifetime earnings. At worst, it leads to dead-end jobs in obsolete technology, imprisoning you in an unfulfilling role with little prospects elsewhere.” - Blake Norish

⏩ Actionable Step: Identify what your ideal career outcome looks like. Where are you today? Where is that person? What are the skills, experiences, network, and teachers that separate you from being that person? What role can give you access to all or most of those things? Use that as your ideal role grading rubric.

MARATHON PACE
They Stayed Consistent

Consistency was key.

Regular networking, skill-building, and a structured job search approach led to success.

Everyone starts their job search with adrenaline and sprints out the gate.

Very shortly, you feel burned out.

I love the quote from Rich Roll, "It’s not the fastest who wins the race, it’s the one who slows down the least.”

The people who saw the fastest results didn’t take two-week vacations or take action only when they felt like it.

They got good sleep, ate well, exercised, and took daily action.

👨 Real Life Example: Graham was a part of a layoff in 2022 and his company connected him with Early. He quickly dove in and took action. Early on, his networking felt exhausting because he wasn’t seeing responses. But, he continued to ask questions, send the messages and low and behold, 2.3 months later he was in a role that matched his ideal job description with nice compensation bump.

🧠 Expert Insight: “I don’t have a formula to pass on. I always did it my own way. Even today, I hold my independence close. It’s what’s most precious to me. Passion. Risk. Tenacity. Consistency. This is my professional history.” - Georgio Armani.

⏩ Actionable Step: The most important contributing factor in your ability to stay consistent is your health. The more you can eat healthy, get good sleep, and exercise regularly the more you’ll be able to keep to a regular schedule. In addition to that, blocking off time at the start of each week as you plan your week will help remind you of what needs to be done and time gate your tasks.

FOLLOW WHAT WORKS
They Trusted The Process

The most successful job seekers understood that finding the right job at the right company is a journey.

They trusted in a structured approach rather than randomly applying to jobs.

The process they followed consisted of:

• Phase 1 - Creating clarity of their next step in the form of an ideal job description that would match their career priorities.

• Phase 2 - Getting confident in their abilities and the impact they drive and reflecting that in their LinkedIn profile and resume.

• Phase 3 - Connecting with people who can help them in their existing network and through cold outreach. Focusing on relationship building.

• Phase 4 - Creating value for each person they interact with.

• Phase 5 - Competing in every interview or networking conversation like it will be their last. Separating themselves in the preparation.

👨 Real Life Example: Evan had left the VC world to run his own business but after a few kids and a change in the market decided it was time to get another full-time-job. The rub was he hadn’t searched for a job in almost a decade. He knew he would be more successful with a process, implemented each of the steps, and received an offer in less than 3 months.

🧠 Expert Insight: “Trust the process. Your time is coming. Just do the work and the results will handle themselves.” - Tony Gaskins

⏩ Actionable Step: If you want your job search to succeed you need a plan. So take the time at the start to understand what you’re going to do. I recommend following the 5 phases above because they have been what have led me and other people to quick and significant success. But whatever you do, create a plan or plan to fail.

The journey to landing a startup job quickly isn't just about possessing the right skills or experiences.

It's equally about mindset, approach, and attitude.

The 10 traits we've discussed are common threads among those who've successfully navigated this path.

• Investing in yourself, whether financially or through time and effort,

• Competing on generosity

• Asking for help

• Putting yourself out there

• Taking quick action and adjusting

• Remaining optimistic

• Having a clear "why"

• Focusing on fit over money

• Staying consistent

• And trusting the process are all critical components of this journey.

Remember, each job search is unique, and what works for one person may not work for another.

However, these traits provide a solid foundation and a guideline that can be tailored to your individual circumstances and goals.

As you embark or continue on your job search journey, consider which of these traits resonate most with you and how you can incorporate them into your strategy.

The right opportunity is out there, and with the right approach, you're well on your way to finding it.

Let’s become career champions together 🏆

Kyle