Start at a Startup?


A group of students from the CalPoly, (San Luis Obispo) Entrepreneurs came to visit my company last week. One line of questioning they pursued was where to begin their careers—should an entrepreneur found their own company right after college, or join a startup and learn how it works before striking out on their own?

I would add into the mix the possibilities of starting your own company immediately, or beginning your career at a larger firm. All these options have positives and negatives—and not just for potential founders. Anyone thinking of jumping into the world of startups should consider if they are ready to move forward, or if they should first scout ahead.

Right Away

If you want to start your own company, then why wait? Do it right now—you don’t need to wait until you’ve finished college. I can think of a couple folks who tried this approach and had some success.

This is one way to find out how serious you are. If you are not willing to commit immediately, why do you believe you will be willing to do so at sometime in the future? You never have less to lose if it doesn’t workout. And, if you start right away, you can tap your college network for cofounders and first employees. You have been building your network of talented people, right?

The best argument against starting immediately is any uncertainty about your product or company strategy. Actually, this is the best argument at any time for not starting a company.

But your concerns about whether you are ready to strike out on your own may be valid. With the right attitude and a little luck, you could learn a lot by working for an existing company.


The closest alternative to starting your own company is to join an existing startup. If you can find an early-stage, fast-moving company with talented folks, you should have good opportunities to learn. It won’t be the same as starting your own company, but it is as close as you can get before you do so.

An amazing number of small companies are fighting to get ahead. Without the right connections, finding one that is truly excellent is tough. Once again, your network matters. Do your research and don’t hesitate to ask for guidance as you look at potential employers. Be prepared to say no to those that are not right for you.

You can “wear many hats” at a startup, but don’t wait for them to be handed out. Ask for responsibilities, then do a great job with them! Then do it again. One of my recent blog posts covered this concept. It is good advice regardless of the company, but opportunities at a smaller company will tend to show up bigger and faster.

Big Co.

The idea that someone who wants to found or work at a startup might first join a bigger company is counter intuitive. But companies of any size can offer worthwhile lessons. A company does not get big if it has not done something right. You can learn from their successes, and identify some traps to avoid. You can dramatically increase your network at a big company.

This may be where you get or refine your amazing idea—the one you need to start your company. It’s not unusual to discover gaps in product or service offerings that Big Co. cannot (or will not) fill. One caution regarding non-compete clauses: In many states (and countries), employment contracts can contain a clause that will bar you from entering into a business or profession deemed to be competing with your former employer. This is one key to Silicon Valley’s success. Non-compete clauses are generally invalid in California! Disclaimer: IANAL

To gain the most valuable experience, pick a great team at a great company. I am not a fan of companies that place you in a position of their choice. Some top companies do this, and you may decide to take the risk. It could work out well—or you could end up in an undesirable role where you have to prove yourself to get where you should have started.

Be careful: big companies can get cozy! If you are succeeding at Big Co., you may find your entrepreneurial yearnings wane. I’ve worked at some great larger companies where I have been willing to stay for many years. In the end, the lure of smaller, nimbler companies has always pulled me away, but that is not true for everyone.

Any Way You Go

Find a place where you can learn from good people. Work smart and hard. Seek challenges. Impress the hell out of people, and build your network. All of this will serve you well. You could try a couple of companies to learn a little more. Start refining your product or service ideas and your execution strategies.

You need to know how to develop your great idea into reality. Pay attention! Lessons are flying by while you are busy working. Consider the companies at which you work before you found or join a startup to be self-paced courses in how to make it happen.

The elephant in the room is that you might really need any job and be forced to take one that is suboptimal. In this case, take the job, make the most of it, and prepare yourself for better opportunities.

Best of Luck

I am just skimming the surface of the pros and cons of working at companies at various stages. If you have an open mind, you can learn almost anywhere. You will never be 100% prepared, but, if you want to be a true entrepreneur, at some point you just have to go for it.

Best of luck!