Since solo founders don’t have to make decisions over anyone, they exercise almost complete control over their startup’s mission.

But you have to pay the cost to be in charge: A shot-caller must be comfortable making decisions under pressure and adept at fundraising, recruiting, onboarding, management… well, everything.

According to Russ Heddleston, who founded DocSend before Dropbox acquired it, lone wolves tend to fare better with investors: His analysis found that one person can raise $3.22 million on average after 42 meetings, but teams of four or more must book 30 sessions to raise $1.7 million.

But fundraising is only part of a founder’s journey. You can’t build a sustainable business if you can’t connect with an investor who can help you find and fill your talent or expertise gaps.


Speaking as a veteran of multiple early-stage startups – I would much rather work at a company run by a team. This usually promotes a collaborative culture but makes making adjustments when needed easier, and the work is less ego-driven.

In a guest post from TC+, Heddleston identifies four factors to consider before deciding to go solo and some ideas for solo founders building support systems.

Full blogline+ items available to members only. Use discount code TCPLUSROUNDUP to get 20% off a one or two-year subscription.

On Tuesday, May 24, at 11:30 AM, I’m hosting a Twitter Space with Silicon Valley immigration attorney Sophie Alcorn.

If you have questions about legally working and living in the US while pursuing an engineering career, join the conversation. Follow @bloglinePlus to get a reminder for the chat.

Thank you so much for reading, and have a nice week!

Walter ThompsonSenior Editor, blogline+@yourprotagonist

How to develop your DTC startup’s data strategy and identify critical metrics?

Most ecommerce startups use the same major platforms and analytics tools to collect data for the dashboards that measure the health of their business.

As a result, most direct-to-consumer companies are making the same mistakes when refining raw transaction data, said Michael Perez, director of growth and data at M13.

The calculation errors captured in platform data can lead teams to miscalculate key metrics, “drastically overestimate the value of their customer lifetime, and overspend on marketing campaigns,” says Perez.

He identifies two common data errors: creating metrics at the wrong level of granularity and using downstream metrics that usually result in data silos.

“We’re generally big fans of plug-and-play business intelligence tools, but they won’t grow with your business.”

Here come the single-digit SaaS multiples

SaaS startups have had a smooth run, but stormy weather is on the horizon in this ongoing downturn.

The days of double-digit revenue multiples are soon coming to an end — public software companies growing just 40% trade at about 10x revenue, meaning startups that can’t sustain that pace could see their valuation multiples plummet to the single digits, Alex Wilhelm found. In its analysis of data from the Bessemer Cloud Index.

“The future will probably hold rounds, flat rounds, and what I expect will be some dramatic implosions.”

To win insurtech 2.0, focus on adoption before growth

According to Jamie Hale, CEO and co-founder of Ladder, the first wave of insurtech startups has focused on driving growth at the cost of managing their underlying risk.

“Focusing on customer experience at the front does indeed lead to rapid growth,” says Hale, “but not focusing on adoption at the back end can lead to a very large number of claims very quickly.”

Hale offers five tips that insurtech startups can use to improve underwriting innovation and improve the overall customer experience.

5 Lessons From ‘Star Wars That Can Transform Startup Executives’ Strategies And Tactics

The ‘Star Wars saga is based on a story structure developed by Joseph Campbell, a writer and literature professor who conceived ‘the hero’s journey’.

Its 12-stage archetype calls for a protagonist who leaves ordinary life behind after hearing the call to adventure – you can imagine why it’s a popular metaphor among tech investors.

According to Scott Lenet, president of Touchdown Ventures, Jedi Knight Obi-Wan Kenobi offers five discreet lessons for founders and investors.

For example, “‘I have a bad feeling about this’ is a recurring joke in the franchise – almost every main character pronounces the line at one time or another,” writes Lenet.

“These are also words to live by for business and startup leaders, as they are emblems of awareness and proactiveness.”


I have been blogging since August 2011. I have had over 10,000 visitors to my blog! My goal is to help people, and I have the knowledge and the passion to do this. I love to travel, dance, and play volleyball. I also enjoy hanging out with my friends and family. I started writing my blogs when I lived in California. I would wake up in the middle of the night and write something while listening to music and looking at the ocean. When I moved to Texas, I found a new place to write. I would sit in my backyard while everyone else was at work, and I could write all day.