Life as a first-time entrepreneur is well documented. Naturally, things change on the next entrepreneurial venture, especially when the first time goes well. Here are a few differences as an entrepreneur on the next venture:
- Culture – Eventually entrepreneurs arrive at the understanding that people trump all other opportunities and challenges in a startup, making a focus on culture from the beginning more commonplace
- Hiring – People want to be part of a team with proven success, making the recruiting process easier
- Rhythm, Data, and Priorities – Whether it’s Mastering the Rockefeller Habits, or some other methodology, the second time around is easier due to having an established management process
- Capital – Raising money is much easier after having a successful exit and investment terms are more entrepreneur friendly
Finding product / market fit, building a customer acquisition machine, and scaling the business are still extremely difficult, regardless of being a first-time or tenth-time entrepreneur. Startups are hard, but having gone through it before makes entrepreneurs on their next venture more confident and more likely to not make the same mistakes.
What else? What are some other differences as an entrepreneur on the next venture?
David Cummings on Startups 
David, really enjoy reading your blog regularly. I think having that first-time success as an entrepreneur makes it more difficult to do it the second time unless that first experience was filled with adversity in the scaling phase (and overcome). The key to repeatable success is the learning that happens in the most difficult of times. Also, having an advisor or mentor who can contribute unbiased opinions and advice is incredibly important and often undervalued.
The Approach. Everything above is solid, and to expand, I think one of the most critical elements to an entrepreneur’s second coming is his/ her approach. You learn so much about what to say, how to say, what to ask, etc. that before anything is really built, the idea is validated, customers are (hopefully) lined up, and essentially, you’ve built a foundation that is more solid and faster than before.
Going through a startup the first time is rough, and you learn a ton. Whether you are successful or you “fail”, you learn a lot so that your next venture has many of its ducks in a row. For example, for me, I know better on researching and getting customers really signed up and bought in for the future. Research here is more prepared interviews (the right questions to ask) and iterations of the idea with prospective buyers and partners.
You won’t know all the right questions and the right way to approach a new idea just from your first, but hopefully with a lot of good learnings, you’ll be able to identify most of them. And if you’re real good and learned from prior, you’ll be in position to heed warnings and be ready to push-through more readily.
I have found a bunch of differences from Round1 (Qloud.com) and Round2 (Kapost):
1. My ambition is higher. We sold Qloud for $8mm. I have no interest in flipping Kapost. I want to build a real, sustainable business
2. Business confidence. The first time around, there are a lot of newness. The 2nd time around, you have more confidence that the decisions you’re making (hiring, board construction, culture, product, tech architecture, leases, etc.) are all easier as you have some experience talking the language and doing it.
Great points, both in your blog post and in comments, certainly a ton learned from successes, failures, obstacles and issues overcome from earlier experience. The key is the wisdom to know exactly how to apply lessons to somewhat different circumstances the next time, and the willingness to take calculated risks again. And how to minimize risks and bet on new approaches and new types of partners than you had before. But as I’m finally getting through formation stage of a new company and team, early on all the excitement of the big vision and disruptive possibilities are there. I know it won’t be a straight line to success, but ignorance is bliss at the start!