Vouch's $45M Series B

Hit Start Media's $600k Pre-Seed

On this episode of How to Raise a Round, we sat down with Theo Miller– founder and CEO of Hit Start Media–to discuss his $600k Pre-Seed. Hit Start is a media production startup focused on creating strategic first-party podcast content, and produces several shows at Carta–including How to Raise a Round. Theo didn’t start his career in tech–he actually was trained as an actor, and was working toward becoming a playwright. When the recession hit in 2008, he taught himself to code and design, and landed a job as a freelance designer. He was hired by Carta–or eShares as it was known at the time– as one of the first five employees. After the company began to rapidly scale, Theo felt that he no longer had a place there. After leaving Carta, Theo explored different podcasting styles with his friend, business partner, and early Carta team member, Zibbie Nwokah. After acquiring clients and regular revenue, the pair realized that Hit Start should be a media company that was software enabled, built for scale. As Hit Start took a more solid shape, Zibbie reached out to their network, finding a significant amount of interest from angel investors. Theo began looking for an investor who could lead his round, and offer some solid experience and advice as Hit Start began to scale. Theo was looking to reach out to Manu Kumar, co-founder of Carta. Manu is the founder and Chief Fire-Starter at the pre-seed fund K9 Ventures, and is regarded as one of the most renowned investors in Silicon Valley. When Theo emailed Manu asking for a meeting, he accepted immediately. From his experience as a writer and performer, Theo recognized that he couldn’t just give Manu a rehearsed presentation and be done with it–he needed to tell a good story above anything else. Manu agreed to come on as Hit Start Media’s lead investor and invest $500k in the company if Theo could secure the next $100k through his own connections. From there, he reached out to executives in his network who agreed to become angel investors. In April of 2021, Theo raised Hit Start’s $600K Pre-Seed round, led by K9 Ventures and filled out by checks from three angel investors. Learn more about Hit Start Media › [https://hitstartmedia.com/]

Eight Sleep's $6M Series Seed

This week on How to Raise a Round we sat down with Matteo Franceschetti, CEO and Co-Founder of Eight Sleep— a sleep fitness startup that sells smart mattresses that tracks users’ sleep cycles, adjusts the mattress temperature, and even uses bluetooth to connect to a smartphone. As a hardware company in a software-dominated space, Eight Sleep’s fundraising journey was full of obstacles. Matteo also used a crowdfunding campaign to prove to investors that customers wanted to buy their product. Eight Sleep’s crowdfund was a massive success, which doesn’t sound like a bad thing—but it created a set of new manufacturing problems. After being accepted into the Y Combinator on their third attempt, Eight Sleep was always changing. As the team scaled and rapidly hit more and more of their goals, Matteo continued adjusting the cap based on demand, so that when his company hit a major milestone it was reflected in the valuation. Although the team already had a couple of checks in the bank, demo day at YC still brought its fair share of anxiety—and with nearly $5 million more to raise, Matteo knew he had to give the perfect pitch. By de-risking Eight Sleep, frequently adjusting his valuation cap, and staying in the fundraising mindset at all times, Matteo and his co-founders have turned an ambitious pajama party crowdfunding event into a massively successful mattress company. Over the next six years Matteo would prove again and again that there isn’t just one way to raise funds—and it’s safe to say that today, with Eight Sleep’s valuation nearing $500 million, that the hard work paid off. In the end, Matteo and his team raised $6 million during Eight Sleep’s Seed round. Learn more about Eight Sleep › [https://www.eightsleep.com/]

Vouch's $45M Series B

On this week’s episode of How to Raise a Round, Josh Weisman sat down with Vouch co-founders Sam Hodges and Travis Hedge to discuss how meeting for coffee became their $45M Series B. Vouch got its start in 2018 and provides startup business insurance for those building the future.  The idea generated a lot of investor buzz, and by the summer of 2019, Vouch had been accepted into the Y-Combinator. The co-founders were laying a solid foundation on which to raise their Series B when Sam got an unexpected surprise. A few minutes into a routine conversation with an investor, he was handed a term sheet. Would it be worth it to sign the preempted term sheet and raise their Series B in a few short weeks? After a phone call with Travis, it was decided: Vouch would accept the term sheet, and had just two weeks to raise. Sam and Travis began jetting around the country to reconnect with the investors, and they quickly realized they couldn’t raise based on their relationships alone. Travis and Sam tranched their round into two closes: the first for investors with an established relationship to Vouch, and the second for smaller-check investors, which brought them a few new angel investors. Based on the strength of their connections, Travis and Sam raised a $45M Series B, with the Y Combinator’s Continuity Fund leading the round. Learn more about Vouch › [https://www.vouch.us/]

The Landing's $2.5M Seed Round

On this episode of How to Raise A Round, we sat down with Miri Buckland and Ellie Buckingham, co-founders of The Landing, a social design platform for interior decorating. Ellie and Miri leveraged their fundraising campaign to test product-market fit, and ultimately used this customer feedback loop to raise a $2.5M seed round. After graduating from Stanford, Ellie and Miri raised an angel round and began beta testing. After a summer of moving furniture around themselves for their end-to-end design model, the pair realized their model was unsustainable, leaving no space to scale. In early 2020, Ellie and Miri put together a pitch deck and began meeting with investors. After several no’s, they decided to make the most of meetings they had by digging into investor feedback. Then, COVID hit. Ellie and Miri used COVID to take a step back from their funding process. After securing an extension from their original angel investor, they set out to redesign their platform based on the feedback collected. Miri and Ellie rebuilt the home furnishing service into the social design platform—and were once again ready to raise. The pair took investors who had offered helpful feedback and added them to their monthly email update list. When they were ready, Ellie and Miri could return with their new and improved product—showing their problem solving chops. By doing reference checks and detailed research into potential investors, Ellie and Miri could be sure they were set up for support and success, ultimately raising $2.5M. Learn more about The Landing › [https://thelanding.app/]

Worklete's $6.5M Series A

On this episode of How to Raise A Round, we sat down with Worklete co-founder and CEO Benjamin Kanner. Benjamin built Worklete as a skill-building application that uses sports medicine to reduce injury in frontline workers, inspired by his father. Benjamin’s father was a professional athlete and a firefighter—and he utilized both skill sets to protect himself from musculoskeletal injuries—and thus Worklete was born. Benjamin took the initial model for Worklete and built it to scale, and saw massive growth in 2017. As business took off, Benjamin realized his current business practices weren’t sustainable — he couldn’t do all the selling himself. Benjamin also needed to raise, and quickly—his wife was expecting, and he needed to be done funding before his first child arrived. Benjamin worked with an advisor to maximize the impact of his raise on both coasts—setting a $5M valuation for his priced round. After polishing his pitch with the warm contacts on the East Coast, Benjamin headed to Silicon Valley. In just four weeks, Benjamin raised $6.5M from seven investors in Worklete’s Series A. The round was made up of Trinity Ventures’ $5M contribution, and a mix of funds from Angel Investors and VCs. Learn more about Worklete › [https://www.worklete.com/]