Small. Then Medium. Then Big. Then HUMONGOUS!


Today I heard of some not-yet-out-of-school wantrepreneurs who believe that they have to promise to build a $billion company to woo investors and be worth their time. My advice: kids, don’t get ahead of yourselves.

Step 1: start by joining a young but vetted startup, say a YC or TechStars company. Those folks will undoubtedly have a year’s worth of funding locked up after demo day, a need for more employees, and you’ll be early enough to get a real birdseye view of all that’s involved in getting something going.

Step 2: You’ll already know now about things like fundraising, building and maintaining corporate culture, what works for you and what doesn’t, and you’ll be more fundable. Go hit a single. Don’t be embarrassed by an early exit, or handing it off to an entrepreneur who is skilled in scaling.

Step 3: Guess what: now you’re a successful, serial entrepreneur. The world is your oyster. Now you can go big. You have connections, you’ll have knowledge, and you’re now picking and choosing who will be in your syndicate.

Think of the great repeat entrepreneurs. Almost always, their exits got bigger with each company.  Before you go Burj, start with a tall or a grande.

3 thoughts on “Small. Then Medium. Then Big. Then HUMONGOUS!

  1. Andrew Ellis Reply

    Some of us entrepreneurs get started much later in life so we don’t have the benefit of rising through the ranks. We press forward with a vision — guided by a lifetime of practical experience, the folks we meet along the way and the knowledge that we glean from the posts of VC’s and Angels. Thank God for talkative, smart bloggers.

  2. marketingjanet Reply

    I would offer a different perspective. After managing a lot of college students and young people, and having been that young person at a startup myself… I firmly believe 90% of new grads, if interested in startups, would be better served working for a later-stage startup (Warby Parker, Wayfair pre-IPO) and learning by being in an environment of a well-run company with a management team that knows what they are doing.

    Early stage companies are still trying to figure out what things they should be doing. That’s really really hard in and of itself. College students and new grads are trying to figure out how to do the “things.” You’re still learning your craft at that point. That too, is really really hard in and of itself.

    To be in a situation where you’re not only tasked with figuring out WHAT a company should be doing, but also HOW to do those things, can be unbelievably frustrating and unproductive for both sides.

    Of course then, there is that 1% that thrives in unstructured environments and knows how to get things done while still learning along the way… and I’m assuming your post is targeted at those crazies. 🙂

    1. Ty Danco Reply

      You’ve made a great case. I’ll think about it, but in my opinion the best reason to work at a bigger company is to learn if you fit in a bigger company. There’s a continuum here–the best answer in any case is if you can find someone great to work with. That’s the key, regardless of size of company, but it’s not always easy to know. At my first job, that key person left 1 month into my job, and it took months to get back the pace of learning what to do–I only saw what not to do.

      Thanks for the terrific comment.

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