As a first-time founder, I worked 16-hour days, skipped my honeymoon, and micromanaged everything. Now, as a second-time founder, I’m doing things completely differently. Here are 5 lessons I’ve learned the hard way:
1. First-time founders care about product. Second-time founders care about distribution. At StackCommerce, I spent too much time building features no one used. Now, I focus on solving clear problems, selling early, and validating with customers before we build.
2. First-time founders hire fast. Second-time founders hire slow. I used to rush to fill roles and paid the price. Now: • I hire freelancers first. • Culture fit is a MUST. • I’d rather wait than make a bad hire. The right hire is worth the time.
3. First-time founders chase growth. Second-time founders chase retention. At StackCommerce, we were always focused on top-line growth. With Onward, we’re focused on: • Customers who stick. • A team that thrives. • A product that solves enduring problems.
4. First-time founders say yes. Second-time founders say no. I said yes to every feature, meeting, and idea early on. Now, I ask: • Does this align with our goals? • Is this a true priority? If it’s not a hell yes, it’s a no.
5. First-time founders burn out. Second-time founders set boundaries. I used to think sacrificing my health and family was the cost of success. Now, I work 8-5, take weekends off, and spend 1-2 months in Europe every summer with my family. Boundaries = freedom.
First-time founders hustle harder. Second-time founders build smarter. These are the lessons I wish I knew my first time around. If they helped, share this thread—and follow @jnpayne for more insights on startups, scaling, and being a 2nd time founder.
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