Mostly advice: When's the best time to join a startup? (2024)

Mostly advice: When's the best time to join a startup? (1)

Before we get started - I made a startling revelation last week. Hot Topic, the counter-culture, grunge, gothic corner of your local mall, is PRIVATE EQUITY OWNED!!! Yeeesh. Talk about being a sellout. That is SOOO not Punk Rock.

As someone who used to (secretly) fit into their demographic (I actually think I still have a Sum 41 tee kickin’ around somewhere), they should have asked me or the guys from Fall Out Boy for advice before going the LBO route.

Speaking of advice…

I asked my network of CFOs, VCs, and Substack writers, as well as our punk rock Mostly metrics readers:

When’s the best time to join a startup?

If you are trying to learn, accelerate your career, and maximize your equity outcome, when do you hop on board?

Weighing the chance of failure, if you had to do it 10 times over, you’d bet: [Series X]…

Here are the best responses I got, along with my own take:

Fit, Happiness, and Tours of Duty

Fit is by far the most important consideration - years of unhappiness shouldn’t be traded for an equity outcome, at least to me.

I would argue a Series B with top-decile type traction is the best risk-reward.

Why? Strong potential for equity growth but the amount of capital raised is “small” enough to not need a massive IPO or exit to enjoy some upside, even in good, but not great, outcomes.

When you asked this, the 10 tries stood out. An under-told story: plenty of folks work for multiple early-stage companies and never make a cent on their equity packages. Your realistic window where you are senior enough and stay long enough to earn real dollars is more like 3 tours of duty, not ten.

Choose wisely!

-Matt Harney and author of

Types of risk, Climbing out of holes, Validating market size

Yo! I’d join a series B. By then you’ve typically eliminated a good amount of product market fit risk and are shifting into taking execution and scale risk. This is where people like us can add the most value!

I’d also want to understand the total liquidation preference stack, and make sure the company isn’t already in a hole. All of the value that comes with climbing out of that hole won’t accrue to you.

And of course - market size. Must be at least a $1B TAM imo.

-Geoff Byron, Biz Ops leader at Workday

Investors as borrowed credibility, Metric related questions, and Red flags

Mostly advice: When's the best time to join a startup? (2024)

FAQs

Mostly advice: When's the best time to join a startup? ›

Go Early, Go Often

What's the best time to join a startup? ›

Joining early, especially at the seed stage, means joining a company that is highly unlikely to exit. If you want the best chances of your equity in a startup being worth more than the tradeoffs you'll be making to get it, the data says to join a startup at Series C, A, or B (in that order).

What is a startup select the best answer? ›

The term startup refers to a company in the first stages of operations. Startups are founded by one or more entrepreneurs who want to develop a product or service for which they believe there is demand.

Why do you want to join a startup answer? ›

I am excited about the opportunity to be a part of a dynamic team that is working towards creating something new and impactful. I also appreciate the potential for growth and learning at a startup, as well as the ability to make a significant impact on the company's success.

What is the right time to startup? ›

There is never the right time to build a company. There is only the “must time” — when founding and running your own business is the only thing you can imagine doing. But too many people start businesses for the wrong reasons and fail themselves and those around them.

Should you join a very early stage startup? ›

Early stage companies are on a mission to transform their industries, and their earliest employees are pivotal in making that happen. Startup employees have the autonomy to make decisions that can shape the future of the company, leaving an indelible and lasting impact.

What is the best month to start a company? ›

January is the best time to form a new business for this exact reason—there's less red tape! First, bookkeeping is much simpler. Rather than keep and close the books for a few weeks of a short year, many entrepreneurs like a clean January 1 start date.

How do I decide to join a startup? ›

How to decide if joining a startup is right for you
  1. Have you done market research to prove the viability of the startup?
  2. Is there potential to make money with this service or product?
  3. What is the customer base?
  4. Is this startup pre- or post-revenue?
  5. What is its current source of capital?
Jul 2, 2024

How to pick a good startup? ›

  1. What is the startup's stage? You can likely figure out the stage of a startup by looking at their latest news and funding announcements on the startup's website or LinkedIn. ...
  2. What is the core technology? ...
  3. What can you learn from the founders? ...
  4. Are you genuinely excited?

What are the first hires in a startup? ›

First 4 roles to hire
  • Product or service developer. Product developers play a central role in creating new products and improving the existing ones to meet customer needs and expectations. ...
  • Sales and marketing. ...
  • Operations and customer support. ...
  • Business development and finance.
Feb 26, 2024

What is the best way to answer why do you want to join? ›

"I'm drawn to this job because of the opportunity for growth and advancement. I'm eager to learn new skills and take on new challenges, and I see this role as a perfect fit for my career goals." "I'm excited about the company's mission and values, and I believe in the work that you do.

What is your main motivation to join our startup? ›

Passion and excitement

A hallmark of startups is their energy and excitement. The newness and potential for success can create a positive, motivating environment that employees enjoy being a part of each day. When everyone shared a common goal of building the business, it enhances employee commitment and productivity.

What makes you a good fit for a start-up? ›

Assessing Your Fit

To work at a start-up, you'll need to do three things you might not have learned in school or in jobs at larger companies: manage uncertainty, push the limits, and think like an owner.

What is the golden rule of startup? ›

Startup metrics should be every founder's true north. We call it KYN (know your numbers). Some founders do it, and some don't.

What are the 7 stages of startup? ›

Key startup growth stages
  • Pre-seed stage. In the pre-seed stage, founders define their business idea and prepare for pitching it to potential investors. ...
  • Seed stage. ...
  • Early stage. ...
  • Growth stage. ...
  • Expansion stage. ...
  • Maturity stage. ...
  • Merger and acquisition stage.
Jul 1, 2024

Is 40 too late for a startup? ›

Assessing Risk, not Age

There's nothing stopping us from trying at any age, only what we are willing to withstand if things don't work out. If we continue to believe we can manage our downside, then we confidently start at any age.

Is 30 too late to start a startup? ›

Most people think startups are a young person's game. That entrepreneurship is for the young, hungry grads who love ramen. But they're wrong. A Harvard study found that the average age of the most successful startup founders is actually 45.

Is series A good time to join a startup? ›

Given these statistics, it's much better to join a company after their Series A or Series B round. You don't have to go through the high probability of failure, your base salary is going to be higher, and the company has probably established a scalable business model to potentially allow you to cash in on your equity.

Is it risky to join a startup now? ›

About 90% of startups fail, with 10% of startups failing within the first year of business. That makes it incredibly risky for employees, especially for those who choose equity in the company over a bigger salary.

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