Ah, the good ‘ole American dream of going to school, studying a profession, and then immediately landing a job in that exact industry. What was once an easy and straightforward process has become harder to navigate in the modern market. Nowadays, more and more people are advocating for becoming your own boss and carving out a corner of the market for yourself. No matter which avenue you pick, when you’re just starting out in your career the highest currency is job experience. Which option is going to offer the better learning experience? Have the better connections? Look better on a resume for future employers? If you want to do both, which option should you go with first? There’s no correct answer, but there are some pros and cons to consider before signing a dotted line.

On Parlor’s Without a Roadmap podcast, Cam and Yonas welcomed Ethan Kopit, a Product Manager at Hubspot! Ethan chatted with the guys about his journey into product, and what it was like joining Hubspot as a PM after starting his own company. They went in depth on whether or not you should start your own company right off the bat, or go work for a more established company. Let’s jump into some of the pros and cons of joining an established company versus building your own from the ground up (and steal some advice from Ethan along the way).

An Established Company

Dolly Parton got it right when she said “working 9-to-5, what a way to make a living”. This is the more traditional option of going into a well-established industry or company and then working your way up through the ranks as you learn and gain applicable experience. Depending on the field you’re in, the landscape can be extremely competitive: there may be hundreds of available jobs or none at all. But once you make it into a company there’s almost always a set career path ahead of you that many people have traversed to become successful. Let’s break down some pros and cons of seeking more stable, established employment.


1. Paycheck: The most obvious joy of joining an established company is that when you receive your contract it comes with a consistent paycheck. Early in your career, this could be an absolute necessity for securing housing and stability in life. It’s a lot easier to plan for life and afford to relocate for a new job coming off the back of a year-long steady paycheck.

2. Mentorship: If you’re working in a company, you’ll most likely have a manager or colleague that has been working in the company for a while. They know the ins-and-outs of the workflows, the idiosyncrasies of the coffee maker, and how to safely navigate team dynamics. More than that though, they can teach you the day-to-day skills required to be successful at your job. As you become a longer term employee, they may help advocate for your promotion or help you network within the industry to find future employment. There’s a built-in opportunity to create a mentor-mentee relationship that can be leveraged for support and career growth.

3. Skill Enhancement: Along with potential mentors and colleagues helping to educate you on new skills required for your job, there’s also training courses that many established companies offer for new and long-term employees. Some companies will even compensate higher education certificates and degrees for employees in exchange for a long-term commitment to the company. Working with established companies can often be a great way to move yourself and your skills before moving on to riskier opportunities.

“I think a lot of the times being a younger person, you can bring something really special and a new perspective to a particular industry. You throw a lot of the things people take for granted out the window and it allows you to approach something with a fresh set of eyes.”  —Ethan Kopit, PM at Hubspot


1. Job Security: It may seem like your job at a larger, more established company is safer, but in actuality, that’s not always the case. An unfortunate reality of the economy (whether you’re looking at the great depression, the economic crash, the housing bubble, or the pandemic) is that job security is never guaranteed. When working in large, established corporations your individual contribution is less likely to be noticed or appreciated. Leaving you open to budget cuts, distant directors, and impersonal bureaucracy. Speaking of bureaucracy let’s hop down to con number two.

2. Bureaucracy: Congrats, you’ve passed all the interviews, talked up how excited you are to create innovation in the market, and are starting off ready to take over the corporate world. Now you get to pour a coffee (or tea), pull up a chair, and wait two weeks for your direct manager to approve that proposal you sent over. Slow moving innovation and even slower steps up the career ladder are unfortunately accurate stereotypes in this case. While you can 100% learn to navigate and get ahead quickly (taking into consideration bias in the workplace), it’s a muscle that requires a lot of exercise.

3. Creative Blocks: Part of moving through an established bureaucracy is learning that established companies have a tried-and-true method of innovation. It’s almost always the slow and steady wins the race mentality. Which makes sense to some extent—large companies tend to avoid quick product shifts to avoid risking customer confusion or alienation, since that could lose shareholder money. However, that means you may be working on one large project for a year before it ever gets released and you get customer feedback on how awesome a job you did. For people that prefer instant gratification and results, smaller companies that allow quicker releases may be more your speed.

Create a Startup

Entrepreneurs get a lot of clout in this day and age. People view them as being risk-taking innovators, changing the face of the marketplace. While this can be true in some cases, not everyone is lucky enough to become the next Steve Jobs. In fact, 90% of new startups fail. So why do so many people take the risk? Dive into some pros and cons of the startup lifestyle listed below.


1. Efficiency: Mean, lean fighting machine. Startups are generally comprised of small teams working at a breakneck pace to accomplish a goal. With limited resources, people tend to focus on core company strengths to drive innovation. This means teams can adapt their product to account for disruptions in the market and quickly release new features for customers.

2. Team Collaboration: Because startups are small ventures, teams overlap and mix as time goes on. Even if you start in one position like as a PM, chances are you’ll be doing some outreach to prospective customers to gauge product market fit and buying interest before the company hires a sales team. While you’ll get to work closely with different teams, the joy of a startup is also the collaboration with customers. Each customer plays an essential role to the longevity of the business so you’ll form close relationships around passions and values with customers.

3. Unique Learning Experience: This collaboration across teams and roles is a unique opportunity to learn new skills. With startups being smaller, you can form stronger relationships and work with people who may have done this before. You’ll get to see the ins and outs of other roles, how your work directly impacts another team, as well as the entire business. Startups often have an all-hands-on-deck mentality that means you’ll likely have the opportunity to work on something you’ve never done before and learn a new skill. Plus, for people who are new to an industry, it’s a fantastic chance to learn what other roles you may want to transition into in the future.


1. Personal Risk: There’s a massive amount of vulnerability associated with starting your own company. Whether you’re working with friends or have managed to acquire a small group of employees, their livelihood depends on how well you can keep the startup running. Not to mention most startups are backed with personal funds and loans, meaning the financial risk extends to yourself and immediate family.

2. Funding: While it’s all fun and games to think up new ideas and how they’re going to change the market, you have to actually build something before you can sell it. Although you may hear about startups taking off and making killer money on the stock market, there’s years of work and funding that was needed to get there. Startups require at least a few months to cover overhead and pay employees. It’s a constant game of finding new ways to cut costs and become more efficient. Even seasoned entrepreneurs who’ve had multiple successful IPOs can still have a hard time securing proper funding and making it last, let alone someone new to the industry that needs to find connections and market a business.

3. Stress: While corporate jobs tout the standard 9-to-5 lifestyle, startups are anything but. Although you can make your own schedule, it’s one of the more demanding jobs in terms of time requirements. Getting something off the ground is a near 24/7 effort to gain enough traction, do enough networking, and receive enough funding to support the endeavor. The relation between highs and lows are also extreme. When the company is doing well, you’re taking over the world—when things are slowing down, you could be facing bankruptcy. It’s a game of extremes so learning to find balance and an objective mindset is essential to succeeding and launching a startup into the stratosphere.


When you’re first starting out in a professional career, there’s always going to be a learning curve. Everything is new and you’re developing and practicing skills for the first time. And that’s okay! So long as you’ve considered the associated risks with either a startup or an established company and have put yourself in the proper position to excel. When trying to make the initial decision between starting your own company and seeking employment there are a couple questions to ask yourself:

  • Do you have an idea that will impact the market? Do you have the means to pursue that goal?
  • What do you want to learn and who do you want to learn it from? Do you have specific people you want to work with or do you want to have a mentor help guide you? Do you learn better in a specific condition, like having established rules to follow or do you like trial by fire and setting your own path?
  • Who do you want to work with? How much does size and culture of the team matter to you? You’ll be spending a large portion of your life with your coworkers, so make sure you’re entering an environment that’s going to have a positive impact.

It’s also important to note that there’s no set answer, nor do you have to choose only one option. You can always choose to gain experience in a company and then branch out to create your own idea or vice versa. As long as you’re actively working to better your skills and gain experience, you’re moving in the right direction.

To hear the interview and learn more about early career advice for PMs, go check out the podcast: https://podcasts.apple.com/us/podcast/ethan-kopit-pm-at-hubspot/id1503231746?i=1000487204301