As a second-time founder, you have a lot of experience and relationships from your first entrepreneurial journey that set you up for success. Some things that repeat founders do differently are:
You can benefit from the network you built while running the previous company.
Fundraising. It’s easier to raise money from investors + a higher valuation.
I remember how difficult it was to get to meetings with reputable VCs when I was new to Silicon Valley. So many more doors open to you, when you are a second-time founder.
Hiring. It’s easier to hire great people.
Many people want to learn from experienced founders.
Prospective customers, investors, and employees will treat you more seriously, knowing that you have a successful (or even unsuccessful) experience of building a company from scratch. First-time founders can be taken lightly by some people.
More experience - fewer mistakes, bc you have an understanding of how to run the business.
But with these advantages came disadvantages:
Speed. Startups with first-time founders usually fail more naturally: if your company ran out of money, you have to close it. I think this motivates you to enter the market faster. Serial entrepreneurs often invest their own money, delaying the launch and wasting the momentum.
When you already made some money you’re motivated to build something bigger than the last time. But luck is often just as important as the personality of the founder.
Many first-time founders have the “never give up” mentality. It often leads to success, albeit at a high cost. Successful founders are often looking for a better work-life balance by delegating more tasks. But you need 100% commitment to succeed.
Basically, repeat founders have advantages and disadvantages, so it’s important to be aware of your strengths and avoid some common mistakes serial entrepreneurs do.