Rob Walling

Rob Walling
Born
💼 Occupation
🏢 Organization	Tiny Seed, MicroConf, Drip, HitTail
Known for	Startups for the Rest of Us Podcast, books on SaaS, various software
Notable work	The SAAS Playbook, Start Small, Stay Small: a Developer's Guide to Launching a Startup, and The Entrepreneur's Guide to Keeping Your Sh*t Together.
👩 Spouse(s)	Dr. Sherry Walling (2001-present)
🌐 Website	robwalling.com

Rob Walling is an American author, software developer, and podcaster who is best known for creating the application Drip and writing books about the software as a service (SaaS) industry. He has written and co-authored books on starting businesses without outside investment, acquiring funding as a small software startup company, the SaaS industry as a whole, and bootstrap funding.

He has authored and co-authored three books on SaaS marketing and business ownership: The SaaS Playbook, Start Small, Stay Small: a Developer's Guide to Launching a Startup, and The Entrepreneur's Guide to Keeping Your Sh*t Together. Walling has founded, co-founded multiple SaaS businesses, the most well-known being HitTail and Drip. He has hosted a podcast called Startups for the Rest of Us since 2010, as well as a podcast called TinySeed Tales.

Personal life

Walling grew up in a household where "money was always an issue". His father was an electrician and his mother was a homemaker. In 2001, Rob Walling married Dr. Sherry Walling, a clinical psychologist and host of the ZenFounder podcast, and co-author to one of his books. As of 2023, they live in Minneapolis, MN and have two boys. They play tabletop games and card games.

Career

Walling taught himself to program when he was 8 years old. He graduated from college in 1998 and spent his first two years in construction before moving into the software industry. He then got a salaried job in software development, and he began consulting and working on side projects from 2002-2009.

MicroConf (2011-present)

In 2011, Walling co-founded a community for bootstrap funders called MicroConf. The first in-person event was in Las Vegas. The company is an online community that also hosts events and conferences in the US, Europe, and remotely. Walling owns the Numa Group, which is an umbrella company for his other companies.

HitTail (2010-2015)

In 2010, Walling acquired a search engine optimization (SEO) analysis product called HitTail, a long tail keyword search tool. He began building mini courses for users of the application, and wanted to promote the courses. When integrating HitTail with email service provider MailChimp, he found it time consuming to capture emails and create an autoresponder for communicating with clients interested in using the search tool. Walling also wanted to capture more information about people who used the website. Walling polled 17 business founders and they expressed a need for a product that solved this issue. The challenge inspired Walling to start his own email automation service that later became Drip. In November 2015, he sold HitTail.

Drip (2012-2016)

In 2012, Walling founded the email marketing platform Drip in California. Walling stated he put approximately $100,000-$150,000 of his own funding into Drip.

Walling frequently references his experience developing and selling the product and business. The application was launched without enough funding and he stated that in the first year he hired too many developers, which caused his company to reach a point where they could only cover 45 days of payroll. In 2015-2016, he spent six months to one year developing a relationship with Leadpages and negotiating the sale of Drip to Leadpages, which happened in 2016.

At the time of the acquisition, the company had approximately 1500 clients and 9 employees. Leadpages raised $27 million in Series B funding to acquire Drip.

TinySeed (2018-present)

In 2018, Walling founded a startup accelerator company called TinySeed in Minneapolis, MN, with Einar Vollset, a former computer science professor at Cornell University. The company raises money and invests in SaaS businesses as an alternative to venture capital. They work remotely and support 20-30 companies at a time. Walling started the company as a response to his difficulties securing funding at Drip, as a way to give back to the community with the intention of helping change the industry The group raises money for early-stage software startups. They focus on companies making less than $1 million in annual revenue.

In 2019, Rand Fishkin of SparkToro invested approximately 10% of their savings into TinySeed's program.

In 2021, TinySeed raised $25 million to fund approximately 200 companies over the following 3–4 years. They announced the next 18 companies in the Spring 2021 Cohort: Aurelius, Breachsense, CloudForecast, CraftyBase, Harbor Plan, Lasso Analytics, Lexgo, Localyser, Monolith Forensics, NewsCatcher, Planifi, Postaga, Rails Autoscale, SecurityStudio, Senior Place, Testable, and Zentake. Recipients of the funding included individuals from Minneapolis, Washington, Utah, New York, Ohio, Massachusetts, and Texas, as well as global software developers from Australia, Israel, Kyiv, Chile, Dubai, London, Paris, and Romania.

In 2022, Walling helped fund Accomplice, an AI tool for image creation founded by former Google employee Adam Powell, by raising $120,000 through TinySeed.

Opinions on startups

Walling is a heavily referenced individual in the SaaS industry. He expresses many opinions on startups, funding, business structure, and how to market businesses as a software developer.

Freemium software business model

Walling was interviewed by the Wall Street Journal in 2012 exploring the pitfalls of freemium business structures. He compared freemium to a samurai sword: "unless you are a master at using it, you can cut your arm off".

Purchasing businesses

Walling told Entrepreneur.com in 2016 about his sale of Drip to LeadPages. He stated that he feels building a relationship with prospective buyers is important for handing off a business to a new owner. He also emphasized the importance of already having customers and a customer base in the sale and acquisition of a business. Walling encourages long-term relationship building and builds relationships within the tech community via podcasts and talks.

Starting a new business

Walling suggests a "validate first" approach to starting a product-based business. In 2023, in an interview with Foundr.com, he stated, "Once I had verbal commitments from 10 people who wanted Drip, we put up a landing page and started building an interest list and broke ground on the code." He encourages people to "validate their ideas" twice - get a verbal commitment, create a landing page, and once the landing page works, create the code for the actual product.

Bootstrapping preference over venture capital

Bootstrapping a business is a subject that Walling speaks about frequently. He compares investors to bosses and suggests that working from any location remotely and keeping a level of freedom with less control to those who might invest in the business is a perk to a low-overhead, nomadic digital business model. According to Walling, "Bootstrapping allows you to retain control of your company." Walling goes into more depth on this subject in his book, Start Small, Stay Small. Walling focuses on how to market a software product without securing venture capital.

Developing alternative marketing strategies

Rob Walling recommends using events and community development, as well as podcasts, as a way to promote and develop a startup. He also recommends using marketing strategies to deviate from the current norm within the industry. When SaaS companies used social media as a norm, he found success in sending clients "a T-shirt and a note" to develop "a personal connection".

Written works

Walling wrote Start Small: a Developer's Guide to Launching a Startup in 2010.

Walling released a free e-book called Start Marketing the Day You Start Coding in 2011.

He co-authored The Entrepreneur’s Guide to Keeping your Sh*t Together with his wife, Sherry Walling, in 2017.

In 2023, Walling wrote and published The SaaS Playbook: Build a Multimillion Dollar Startup Without Venture Capital. The book firmly explains his stance against the startup ecosystem's overreliance on venture capital as well as how to bootstrap a business, and the reasons for doing so. Several SaaS industry professionals gave testimonials on the SaaS playbook, including:

• Courtland Allen, Indie Hackers founder;
• Patrick Campbell, ProfitWell co-founder;
• Jason Cohen, WP Engine founder;
• Rand Fishkin, SparkToro co-founder;
• Peldi Guilizzoni, Balsamiq CEO and founder;
• Noah Kagan, AppSumo CEO;
• Dharmesh Shah, Hubspot founder/CTO;
• Laura Roeder, Paperbell founder;
• Derek Sivers, CD Baby founder and author of Anything You Want;
• Adam Wathan, Tailwind Labs founder.

Podcasting

In 2010, Walling started the podcast Startups For the Rest of Us. They recorded their 687th episode in November 2023. Walling often hosts his own episodes, called Rob Solo Adventures.

In October, 2019, he began hosting the podcast TinySeed Tales, in which he interviews new entrepreneurs and recent startup ventures.

Rob Walling has been a guest speaker on several podcasts, such as:

• Agency Mavericks
• Bootstrapped Stories
• Built to Sell
• Everyone Hates Marketers
• Indie Hackers
• Indie Bites
• Know Your Team
• My First Million
• Rogue Startups
• Startup Slingshot
• The Foolish Adventure Show on Internet Business Radio
• The SaaS Podcast
• WP-Tonic Show

References

This article "Rob Walling" is from Wikipedia. The list of its authors can be seen in its historical and/or the page Edithistory:Rob Walling. Articles copied from Draft Namespace on Wikipedia could be seen on the Draft Namespace of Wikipedia and not main one.

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