How to Raise a Round


How to Raise a Round is Carta’s podcast about one of the most difficult parts of any startup founder’s road to success: raising money from investors. Each episode, host Josh Durst-Weisman sits down with new and veteran founders as they recount the highs and lows of raising their most memorable round. They’ll share the mistakes they made, the tips they learned, and how they navigated their unique journeys so that when you go to raise a round, you’ll know where to start.

Introducing How to Raise a Round
Trailer 2 min 5 sec

All Episodes

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 ›

Nov 19

30 min 39 sec

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 ›

Nov 5

28 min 4 sec

CogniCor founder and CEO Dr. Sindhu Joseph completed her PhD in AI. After graduation, the first-time founder created a digital assistant platform for financial services and raised an unconventional $1M seed.Her business philosophy is predicated on trusting her instincts, which is why her family was an integral part of her initial pitch. Despite never pitching before, Sindhu nailed one of the most important components: a compelling story.After securing her initial check, Sindhu began her seed round. She was pioneering a new product market and turned to angel investors. She created a term sheet using a template and sent it to all of her contacts—between 200 and 300 interested parties—betting on the strength of the personal connections she had with her contacts.Her optimism paid off. Sindhu’s raise was oversubscribed— she had $2M in offers when she was looking to raise $1M. In the end, her $1M seed was funded by a handful of angel investors, one VC, and one corporate accelerator.

Oct 22

26 min 12 sec

Christina Ross, the Founder and CEO of Cube, left behind a CFO position after working in finance for 16 years to dive deep into creating her own company. With two young children at home, no funds, no team and no solid plan of attack, Christina was feeling the pressure to succeed.Before she had even begun to build out her pitch deck or product, investors were reaching out to her to set up meetings. As a first time entrepreneur, Christina followed advice from a colleague to take the meeting anyway. Before she even knew it, she had started her first round of funding.As momentum built from potential investors, Christina made the decision to invite potential investors to participate in an investors update list. In doing so, she was able to recommit her effort to building her product, and keep these investors in her line of sight.When it came time to raise her $1.25M pre-seed round, Christina was able to rely on her already robust investors network, while making sure she never entered a meeting without a pitch, a product, and people to pay for it.Learn more about Cube ›

Oct 8

28 min 9 sec

As a first-time founder, Nico Simko, the CEO of on-demand pay provider Clair, found that it was easy to be wooed by investors. It was simplicity and restraint that kept his head in the game through the emotional rollercoaster of fundraising during the tumultuous early stages of a global pandemic. As the stock market succumbed to volatility not seen for over a decade, Nico stayed the course, navigating his company through a seed round of $4.5 million that included heavy hitters such as Michael Vaughn, the former COO of Venmo.Simplicity and confidence were among the most important characteristics Nico found to be of assistance during his funding journey, which also included a $500,000 pre-seed. With institutional investors inundated with pitches and paid to poke holes in business models, it’s the founder’s job to simplify their story and de-risk the business. In a delicate balancing act, they must display confidence and logical thinking without over-negotiating.One of the things you learn as an entrepreneur, Nico says, is that you just have to keep going, “even if you feel like you’re the unluckiest person in the world.”Learn more about Clair ›

Sep 24

30 min 5 sec

After fielding endless criticism and navigating a pivot, Craig J. Lewis, Founder and CEO of gig economy payroll platform Gig Wage, found success in perseverance. The Dallas-based company raised a $2 million seed round in November 2018. But the road there was littered with potholes.A few years ago, Gig Wage was at an inflection point. It had gone through a three-quarters-of-a-million pre-seed working on its initial idea, and Craig felt a pull from angel investors to quit. However, there was a glimmer of hope when a new focus for the company came into focus. Craig began navigating his team through a pivot, heeding signs from the universe that he was on the right track when he found a contractor willing to write the first lines of code and a yoga studio willing to pay Gig Wage to payroll its instructors.That “peek into possibility,” as he calls it, created the traction Gig Wage needed for its next round. In this episode, Craig shares this key takeaway from his funding journey: even the experiences that seem like failures can be wins.Learn more about Gig Wage ›

Sep 10

24 min 22 sec

After quitting a comfortable job in Silicon Valley to dive into her lifestyle startup, Brightly, Laura Wittig found herself in a world of unknown with the start of a global pandemic. The in-person component of Brightly’s Snap Inc. accelerator program was abruptly cut short, and she, along with all others attempting to raise in the summer of 2020, had to adjust to a new virtual dynamic with advisors and potential investors.Wittig says she felt disadvantaged as a female founder, which she said invited more scrutiny during pitch meetings compared with founders who looked more like the investors sitting on the other side of the Zoom meeting. But she found a helpful ally in the Female Founders Alliance, which runs a program called Ready Set Raise that supports female founders during fundraising.If she could offer advice to other first-time founders, it would be this: never give up. Sometimes you might feel like you’re the only believer. It might wear on you. But once you get that lead investor and your first meaningful check, things will start to fall into place.Learn more about Brightly ›

Aug 27

29 min 27 sec

Shaan Hathiramani sat in a comfortable position in early 2020. He was convinced he had at least another year until he had to raise Flockjay’s Series A after an early 2019 $3 million seed backed by tennis star Serena Williams and actor Will Smith. A few months later, however, the pandemic shut down life as we knew it, and Shaan, Flockjay’s founder and CEO, had to reevaluate.After the fog of this initial reaction started to clear, however, Shaan began to realize that Flockjay was uniquely positioned to succeed in this new normal. Flockjay was already a fully remote sales academy, and while hiring for sales reps at major technology companies temporarily ceased at the start of the pandemic, it eventually revived as software companies expanded their teams to meet the intense demands of a suddenly distributed global workforce. That meant that there was demand for talented sales reps—which was Flockjay’s specialty.Learn more about Flockjay ›

Aug 13

29 min 56 sec

Filip Victor, Founder and CEO of identity verification company Mati, raised a $13.5 million Series A in 2020, less than a year after closing an initial Seed round. An immigrant from Poland, Filip launched Mati in 2016 to help people more easily verify their identity so they could access things like financial lending products and car rentals without the extensive paperwork typically required to evidence their identity. After closing Mati’s Seed round and expanding from one to two countries, and then into Latin America, he realized that Mati would need more money—and fast—to maintain their rapid growth.Learn more about Mati ›

Jul 30

27 min 43 sec

Real founders. Real stories. Carta is proud to introduce How to Raise a Round, launching July 30th.

Jul 16

2 min 5 sec