Advantages Of A First-Time Founder

Repeat founders may have more experienced advisers and startup friends to consult, but weighing their opinions can slow decisions. Michael says advice from startup experts can also crowd out conversations with potential customers, who can confirm whether a real problem exists. Harj describes taking longer to commit to an idea for his second startup.

Harj says repeat founders can choose ideas based on how impressive they sound at dinner or drinks, and may overlook small markets that can grow or expand. First-time founders may feel freer to pursue ideas they find interesting, even if they initially sound unglamorous. The group also says first-time founders can find early wins more exciting, while repeat founders may take milestones such as the first paying customer for granted.

First-time founders may have a harder time raising money and hiring, which can push them to build a stronger product and sell it directly. Repeat founders may have easier access to funding, beta users, and press, which can make it easier to coast early. They may also receive less candid feedback from investors and friends because those relationships have become valuable.

Repeat founders can benefit from financial independence, especially when it lets them take a longer view instead of focusing on short-term survival. Their fundraising experience can also help with capital-intensive businesses such as SpaceX, Opendoor, and Boom, though the group says most software startups do not win through access to capital alone. Deep experience in a market can help too: Brad points to Parker Conrad applying HR software expertise from Zenefits to Rippling.

Brad cautions first-time founders to distinguish the facts of a previous founder's experience from their opinion about a market, since a failed attempt can color that opinion. The hosts encourage first-time founders not to assume a repeat founder competitor will win. They close by noting that Google, Facebook, and Microsoft were started by first-time founders.