Shows
Success Story with Scott D. ClaryLessons - The Brutal Truth About Fundraising | Russ Heddleston - Built & Sold DocSend for $165M➡️ Like The Podcast? Leave A Rating: https://ratethispodcast.com/successstory
In this "Lessons" episode, Russ Heddleston, founder of DocSend, breaks down the harsh realities of startup fundraising and what truly separates successful founders from the rest. Drawing from his experience building and selling DocSend for $165M, he reveals why timing a raise is less about fixed milestones and more about credibility, vision, and momentum. Learn how simplicity in your pitch deck earns investor trust, why clarity always beats complexity, and how to approach different fundraising stages with confidence. This conversation cuts through the noise to deliver...
2025-11-0611 min
Venture with GraceRuss Heddleston, Distill & DocSend CEO on SaaS Exits & Scaling to $45M ARRRuss Heddleston is the CEO of Distill, having previously founded and sold DocSend for $165 million with $15 million raised, scaling it to over $40m in ARR. Previously, he started and sold an HR tech startup Pursuit to Meta. Russ holds a BS and MS in Computer Science from Stanford and an MBA from Harvard. His work on identity at Meta and his passion for intuitive product design drive his commitment to Distill.Topics: Designing products for virality in enterprise SaaSStructuring teams for speed without sacrificing qualityHiring in the early vs. growth stages#StartupExits #SaaSFounders #VentureCapital #AcquisitionStrategy #ScalingStartups
2025-08-171h 03
The NFX PodcastHow Running Out of Money Made DocSend a $165M Success w/ Russ HeddlestonRuss Heddleston, founder of DocSend, shares how nearly going bankrupt forced them to rethink everything—turning a failing startup into a product-led rocket ship that Dropbox bought for $165M. From spreadsheets of startup ideas, to the painful lessons of chasing enterprise sales, to doubling their prices and watching conversions skyrocket, Russ breaks down the hard truths behind building a breakout SaaS company. Plus: why he wishes he hadn’t sold, and what he’s doing differently with his next startup.
(0:00) Introduction of Russ Heddleston
(0:40) Russ Heddleston's early career and founding Docsend
(2:02) Microsoft internships and Maru Networks experience
(4:38) Ideation and approach to sel...
2025-07-161h 06
The Startup CEO ShowDocSend's Roadmap: From VC Funding to Dropbox Acquisition with Russ HeddlestonLooking for expert insights on startup success and leadership strategies for CEOs?🚀 Subscribe to Mark MacLeod's Newsletter: markmacleod.me/newsletter------------------Tired of meetings that should've been emails?Fellow's AI Meeting Assistant is your solution—transcribing, summarizing, and streamlining your workflow by connecting with your calendar and productivity tools.Enhance your productivity today: fellow.app------------------------------In this episode of The Startup CEO Show, host Mark MacLeod interviews Russ Heddleston, former CEO of DocSend, to explore the nuances of startup acquisitions and creating market value. Russ...
2024-08-1948 min
High StakesHow This Entrepreneur Sold His Startup To Dropbox For $165M | Russ Heddleston Imagine thinking your startup is doomed, only to be acquired for $165M.On this episode of High Stakes, Russ Hiddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox.In this chat with Managing Partner Paige Soya, they discuss funding, exits, Russ’s next venture, Distill (hint: think Wikipedia but for company and people summaries).
2024-08-1529 min
FFF (Founders, Funders, & Friends)FFF EP. 8 Russ HeddlestonJoin us in this insightful episode featuring Russ Huddleston, a three-time founder best known as the co-founder and former CEO of DocSend, a successful document sharing platform acquired by Dropbox for $165 million. Russ shares his entrepreneurial journey, key lessons from his experience with DocSend, and his new venture, Distil, which utilizes AI for generating in-depth reports on individuals and companies. In conversation with Olive Shum, founder and managing partner at Cuda Management, Russ discusses the evolution of DocSend, the challenges of product-led growth, and insights into leveraging LLMs for innovative solutions. Don't miss this deep dive into the world...
2024-07-2457 min
M&A ScienceThe Challenges of Sell-Side M&ARuss Heddleston, Co-founder & former CEO, DocSend Every owner loves their business. This makes selling their company even harder than it already is. But aside from the emotional turmoil that founders go through every exit, there are also a lot of intricacies included in the process. In this episode of the M&A Science Podcast, Russ Heddleston, Co-founder & former CEO of DocSend, discusses the challenges of sell-side M&A. Things you will also learn in this episode: Considerations in Potentially Selling a Startup Challenges of sell-side M&A K...
2024-01-3156 minM&A ScienceThe Challenges of Sell-Side M&ARuss Heddleston, Co-founder & former CEO, DocSend Every owner loves their business. This makes selling their company even harder than it already is. But aside from the emotional turmoil that founders go through every exit, there are also a lot of intricacies included in the process. In this episode of the M&A Science Podcast, Russ Heddleston, Co-founder & former CEO of DocSend, discusses the challenges of sell-side M&A. Things you will also learn in this episode: Considerations in Potentially Selling a Startup Challenges of sell-side M&A K...
2024-01-3156 min
The Sales EvangelistRuss Heddleston | Surviving Enterprise Sales In a Tight EconomyRight now, more so than ever, it is critical for salespeople to learn how to navigate in a tight economy. On today’s episode of The Sales Evangelist, our host, Donald Kelly, talks with the co-founder of DocSend, Russ Heddleston, about how to listen more, use the prospect's language, and how do ONE thing well for them. Why won’t order-takers survive in a tight economy? Over the last few years, more and more order-taking roles are being pushed to automation. The role of the salesperson is changing because of the amount of competition and vendors. What...
2022-11-1128 min
Sit Down StartupDocSend’s Russ Heddleston on the importance of getting product pricing rightSince launching at New York’s TechCrunch Disrupt back in 2014, DocSend was acquired by Dropbox in March 2021 and has brought on over 20,000 customers. In our Season 5 opener, Adam sat down for a virtual coffee with Co-Founder Russ Heddleston to get the lowdown on: How word of mouth is still important to achieve growth Using customer feedback as a base for making improvements Why founders should monetize their products from the get-go
2022-05-0418 min
The Full Ratchet (TFR): Venture Capital and Startup Investing DemystifiedInvestor Stories 235: What's Next (Tamaseb, Ebinger, Heddleston) On this special segment of The Full Ratchet, the following Investors are featured: Ali Tamaseb Jonathan Ebinger Russ Heddleston Each investor discusses sectors, drivers and/or trends that may have significant impact in the future and are potentially positioned for outsized-returns. Did you miss our guests full length episodes? For other great episodes, go to The Full Ratchet blog and catch up! Also, follow us on LinkedIn (https://www.linkedin.com/company/27155166/) and Twitter (https://twitter.com/TFR_Pod).
2022-03-1706 min
The Full Ratchet (TFR): Venture Capital and Startup Investing DemystifiedInvestor Stories 231: Lessons Learned (Paxhia, Wilkins, Heddleston) On this special segment of The Full Ratchet, the following Investors are featured: Emily Paxhia Tony Wilkins Russ Heddleston Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach. Did you miss our guests full length episodes? For other great episodes, go to The Full Ratchet blog and catch up! Also, follow us on LinkedIn (https://www.linkedin.com/company/27155166/) and Twitter (https://twitter.com/TFR_Pod).
2022-02-1708 min
Success Story with Scott D. ClaryRuss Heddleston, Co-Founder and CEO at DocSend | Best Fundraising Strategies For Growing Your Business➡️ Like The Podcast? Leave A Rating: https://ratethispodcast.com/successstory➡️ About The GuestRuss Heddleston is the Co-Founder and CEO of DocSend. He was previously a product manager at Facebook, where he arrived via the acquisition of his startup Pursuit.com, and has held roles at Dropbox, Greystripe, and Trulia. He sold DocSend to Dropbox for $165M in 2021. He holds an MBA from Harvard and an MS in Computer Science from Stanford.➡️ Talking Points00:00 - Intro01:02 - Russ Heddleston’...
2022-02-0655 min
The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified311. Founding DocSend, Creating a Winning PLG Motion, and Data From 1000's of Pitch Decks (Russ Heddleston)
2021-12-0639 min
The AFT podcast: At the Forefront of Transactions | Payments | Fintech | Pay-tech | BankingRaising $200k through a Twitter post. By Alex Simon with EludeAlex Simon, CEO Co-Founder of Elude in this episode talks about the new strategies that modern founders can employ while fundraising for their startups. We also spoke about some key things that founders should have on hand before starting to raise and about other things that I forgot to write down.
Alex' LinkedIn: https://www.linkedin.com/in/alexnsimon/
Elude website: https://elude.co/
Episode with the founder of DocSend: https://www.fundraisingradio.com/Russ-Heddleston/
70% off (for less than a month) Fundraising Radio's course on how to get in front of...
2021-12-0532 min
The AFT podcast: At the Forefront of Transactions | Payments | Fintech | Pay-tech | BankingDocSend - how increasing prices increased conversions. By Russ Heddleston.Russ Heddleston, Co-Founder and CEO talks about the story of DocSend and how the decision to increase their prices led to an increased conversion rate for their customers and how exactly this magic worked. We've also discussed how DocSend became so essential for the startup founders and how was the product taking shape. In this episode Russ touched onto the acquisition of DocSend by Dropbox and explained how exactly they got to a $150 million acquisition with just $15 million raised.
Russ' LinkedIn: https://www.linkedin.com/in/heddleston/
Russ' Twitter: https://twitter.com/rheddleston
D...
2021-11-1330 min
The Yaro Podcast(EP22): Russ Heddleston, Co-Founder DocSend, Sold To Dropbox For $165 MillionRuss Heddleston is the co-founder and former CEO of DocSend, which was acquired by Dropbox for $165 Million in early 2021. Russ currently works at Dropbox continuing the vision he had for DocSend.
During this interview we hear how Russ went from studying at Stanford, to working at a startup called Greystripe, then as an intern at Dropbox, and then launching his own startup Pursuit.
Pursuit was later acquihired by Facebook, where Russ continued to work for two years. He shares some interesting insights into why Pursuit didn't take off and the lessons learned, which he then...
2021-10-0750 min
Square One: Conversations with the Best in Business104: Russ Heddleston, Founder & CEO of DocSendToday we’re joined by Russ Heddleston, Founder & CEO of Docsend. DocSend is one of the most ubiquitous document-sharing products in the tech industry today. What started out as a simple product to send links has turned into a holistic and robust suite of workflows, privacy settings, and analytics for documents. So much so that large software companies have taken notice - Dropbox recently acquired DocSend for $165 million.Russ and I chatted through the founding story of DocSend, how they grew the business through product-led growth, interesting insights learned from being on the other side of 1000s of...
2021-08-2330 min
Sand Hill RoadE27 Replacing PDF attachments one Docsend at a time with founder and CEO Russ HeddlestonIn this episode, Erasmus Elsner is talking to Russ Heddleston, founder of Docsend. The episode was recorded one month before the announcement that DocSend would be acquired by Dropbox for $165m.
00:00 Intro
00:37 What is Docsend
01:51 Selling Pursuit to Facebook in a talent acquisition
04:12 Leaving Facebook and starting Docsend
07:03 Product idea
09:00 Fundraising for Pursuit
12:53 Fundraising for Docsend
14:17 Series A
17:34 Docsend product
20:39 Initial startup client segment
22:29 Docsend fundraising network
25:20 Expanding from initial client segment
29:51 Docsend Spaces
33...
2021-05-2945 min
Funded | How They Raised MillionsF&F Round: 2020 Funding Trends with Russ Heddleston of DocSend (FF01)This is Funded's first ever Friends & Family Round! With so many listeners asking questions about things they hear in episodes or about the fundraising market in general, we decided to launch this sister show to give more insights with a little help from our friends.
In this episode, Russ Heddleston the CEO of DocSend gives us a very unique view into 2020 trends via his company's recently released Startup Index Report. This report leverages aggregated and anonymized data of pitch deck activity to show things like how many investors need to be pitched before successfully raising. So much of 2020 was a...
2021-01-2120 min
DocSend CEO Russ Heddleston on pitch deck insights, leaning into criticism & more | E1161Check out DocSend: https://www.docsend.com
Check out DocSend's Fundraising Network: https://www.docsend.com/fundraising-network
FOLLOW Russ: https://twitter.com/rheddleston
FOLLOW Jason: https://linktr.ee/calacanis
2021-01-131h 08
The SaaS Podcast - SaaS, Startups, Growth Hacking & Entrepreneurship273: DocSend: A Case Study in Product-Led Growth - with Russ HeddlestonRuss Heddleston is the co-founder and CEO of DocSend, a SaaS platform that lets you securely share your documents with real-time control and insights.The SaaS Podcast is sponsored by:Gusto, an easy, online payroll and benefits service built for modern small businesses. In other words, a people platform - one place to pay and take care of your hardworking team.Exclusive Offer - Get 3 Months Free!Show Notes:https://saasclub.io/273Learn More About SaaS Clubhttps://saasclub.ioBecome a Premium Member:http://thesaaspodcast.com
2020-12-1745 min
The SaaS Podcast: Build, Launch & Scale Your SaaS273: DocSend: A Case Study in Product-Led Growth – with Russ HeddlestonRuss Heddleston is the co-founder and CEO of DocSend, a SaaS platform that lets you securely share your documents with real-time control and insights.The SaaS Podcast is sponsored by:Gusto, an easy, online payroll and benefits service built for modern small businesses. In other words, a people platform — one place to pay and take care of your hardworking team.Exclusive Offer - Get 3 Months Free!Show Notes:https://saasclub.io/273Learn More About SaaS Clubht...
2020-12-1748 min
The Insider's Guide To FinanceHow to Properly Raise Capital (Backed by Data) w. Russ HeddlestonToday we’re joined by Russ Heddleston, Co-Founder and CEO of DocSend. DocSend is an application that is increasingly used by the finance industry for sending documents securely like pitch decks. It can also create secure and tracked file sharing spaces, or data rooms. However, this episode is not about DocSend. Today, Russ will be sharing with us his very interesting Silicone Valley career. Some may even say that Russ has lived the tech dream, from Stanford and Harvard degrees, to selling his first company to Facebook, and now on to launching DocSend, he has been making all of th...
2020-08-0740 min
Bowery Capital Startup Sales PodcastContent Effectiveness During COVID-19 with Russ Heddleston (DocSend)Russ Heddleston, CEO of DocSend, joins the Bowery Capital Startup Sales Podcast to discuss "Content Effectiveness During COVID-19."
2020-05-0135 min
The Future of WorkThe Startup Path to the Future vs. Enterprise ModernizationThe pros and cons as big companies try to modernize vs. new companies spring up. Is it easier to build AAI from scratch or incorporate it into existing systems?
Panelists:
Amrish Singh (Metromile)
Genevieve Wolff Jurvetson (Fetcher)
Jessica Lessin (The Information)
Russ Heddleston (DocSend)
2019-10-2320 min
Grow with Quora45% of Our Social Media Traffic Comes from Quora - DocSendOur guest this week is Russ Heddleston the Co-founder and CEO of DocSend. Tune into to learn why he considers himself an average user who is learning the ins-and-outs of Quora. This is a great episode for everyone who is looking to get started on Quora or invest more time on the platform.
A few insights from the episode:
The snowball effect of how he earned 1 million views on his answers
Quora is driving 45% of DocSend's social media website traffic
Why investing more time in Quora makes sense
If you liked this interview make sure...
2019-08-2000 min
The OperatorsS1E1: Enterprise Sales w/ DocSend CEO Russ Heddleston and Acceleprise General Partner Whitney SalesThis week’s edition of The Operators features Whitney Sales, a general partner at Acceleprise, the leading enterprise SaaS accelerator, and Russ Heddleston, founder and CEO of DocSend, a fast rising document management and sharing product.
Whitney brings sales experience from Loopnet, Meltwater, SpringAhead/Tallie, and People Data Labs, before starting her own sales consultancy aptly named “The Sales Method.” Russ brings experience from founding and selling his first company to Facebook, before becoming the first sales person of the second company he founded, DocSend.
If you’ve ever had to convince anyone of anything, or are int...
2019-06-1759 min
14 Minutes of SaaS - founder stories on business, tech and lifeSelf-Service for Starters - Russ Heddleston, 3 of 3Part 3. Russ Heddleston, CEO of Docsend talks about co-founders being on a similar financial footing before starting, and on whether to target small business with self-serve first in B2B SaaS
2019-05-2900 min14 Minutes of SaaS - founder stories on business, tech and lifeMobile First is Overrated - Russ Heddleston, 2 of 3Part 2. Russ Heddleston, CEO of Docsend (founded 2013, raised $10M), chats about counter-intuitive observations around fund raising pitch decks and whether voice interfaces will kill Docsend
2019-05-2900 min14 Minutes of SaaS - founder stories on business, tech and lifeMobile First is Overrated - Russ Heddleston, 1 of 3Russ Heddleston, CEO and Co-Founder of DocSend (founded 2013, $10M raised), talks about whether you should startup with friends and why mobile first strategies can be over-rated in B2B SaaS.
2019-05-2900 min
2018-12-1117 min
2018-12-1014 min
The a16z Showa16z Podcast: When Organic Growth Goes Enterprisewith Martin Casado (@martin_casado), Andrew Chen (@andrewchen), Russ Heddleston (@rheddleston), and Hanne Tidnam (@omnivorousread)
What happens when the bottoms up, organic growth usually associated with consumer companies starts to go.... enterprise? Part of our continuing podcast series (you can listen to part one on user acquisition and part two on engagement/retention) on growth, this episode explores the increasing trend of enterprise growth shifting to be more "bottoms up" -- with a16z general partners Martin Casado and Andrew Chen, and DocSend CEO and co-founder Russ Heddleston, in conversation with Hanne Tidnam.
So what e...
2018-08-2529 min
Founder Coffee - Intimate SaaS Chats007 Russ Heddleston - DocSendFor this seventh episode, I had a chat with Russ Heddleston, Co-Founder of DocSend, the leading document tracking company. After growing up in South Dakota, and prior to starting DocSend, Russ had quite the track record. He worked at Microsoft, Dropbox, and Conversant. And he sold a company to Facebook.
I first heard about Russ and DocSend when he was featured on TechCrunch. During our chat, we talk about what TechCrunch meant for him, building a great product, how to hire a VP of sales, and how he refused to join the Bachelorette when starting off with DocSend.
Read the...
2018-06-1252 minFounder Coffee007 Russ Heddleston - DocSendFor this seventh episode, I had a chat with Russ Heddleston, Co-Founder of DocSend, the leading document tracking company. After growing up in South Dakota, and prior to starting DocSend, Russ had quite the track record. He worked at Microsoft, Dropbox, and Conversant. And he sold a company to Facebook.
I first heard about Russ and DocSend when he was featured on TechCrunch. During our chat, we talk about what TechCrunch meant for him, building a great product, how to hire a VP of sales, and how he refused to join the Bachelorette when starting off with DocSend.
Read the...
2018-06-1252 min
The SaaS Revolution ShowThe DocSend Growth Story with Russ HeddlestonThe DocSend Growth Story with Russ Heddleston by The SaaS Revolution Show
Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world...
2017-03-1628 min
Valley Talks – stories of Silicon Valley StartupsGetting acquired by Facebook and raising $8M on a new startup!Russ Heddleston, CEO of DocSend – an analytics tool that tracks viewership data after sending documents, is taking Silicon Valley by the storm! His first startup Pursuit – a social referral program – got acquired by Facebook within the first year! He worked for Facebook for over a year as a Product Manager for Pages. It didn’t take him long until he started another business. To keep the ball rolling, he partnered with August Capital and raised 8 million dollars for DocSend!
Sounds like a dream, huh? So how did he do this? What are his strategies? Fortunately for us, Russ speaks about every de...
2016-08-3100 min