Own Pain Startups

Wingman is a conversation intelligence platform that helps sales teams improve performance through real-time coaching, call recording, and pipeline insights. Founded by Shruti Kapoor and two co-founders from Google, the company struggled initially with 40 cold outreach meetings yielding zero sales, but pivoted to an inbound strategy leveraging online communities and word-of-mouth. By focusing on low-friction features and customer advocacy, Wingman grew to over 300 customers and mid-seven-figure revenue before being acquired by Clary in 2022 at a 15-20x multiple.

Merge is a unified API platform that allows B2B companies to add hundreds of integrations to their product with a single integration. Founded by Gil Fai and Shen-Ci in May 2020, the company raised $4.5M seed funding within months and grew to multiple seven-figure ARR through early customer validation, word-of-mouth, and aggressive SEO/content marketing. The company has raised $74.5M total (including $55M Series B in Oct 2022), now has 65 employees and 4,000+ customers, and achieved 30X ARR growth in the 12 months leading up to Series B.

Alasant is a white-label community app platform for master plan residential developments, founded in 2017 after a major Southern California developer approached April LeMond and her co-founder Mike to build a mobile app. Starting with Rancho Mission Viejo, the app achieved 90% adoption within 90 days, and they pivoted from a one-off project to a scalable product. Today, with $2M ARR, 82 communities, 200K+ active users, 100% renewal rates, and a bootstrapped business model, Alasant has built a sustainable, highly-focused vertical SaaS business by deeply embedding in the master plan community industry.

Hint Health is a membership management, billing, and payment platform for direct primary care, urgent care, and specialty practices. Founded in 2014 by Zach Haldsworth and Graham, the company landed its first paying customer within 30 days through cold calling and personal outreach, expanded to 10 customers in 3-4 months, and has grown to nearly 1,000 customers handling over $500 million in annual payments. With ~40 employees and close to $10 million ARR, Hint has raised $60 million across four funding rounds and drives growth primarily through word-of-mouth, partnerships, and community-building events.

Stravito is a Swedish-based knowledge management platform founded in 2017 by Thor Olof Filogen and three co-founders that helps global enterprises centralize and democratize access to market research and consumer insights. The company spent 6 months validating the problem through interviews with companies like Unilever, Procter & Gamble, and Coca-Cola before writing any code, then took 8 months to build an MVP. Stravito grew by focusing on early adopters in the FMCG segment, implementing founder-led sales, and leveraging segment-specific marketing campaigns; the company has raised $23M in funding and serves Fortune 2000 clients including Comcast, Electrolux, and McDonald's.

Bordable is a board management SaaS that centralizes communication, documents, meetings, and governance for nonprofit and for-profit boards. Founded in 2016 by Jeb Banner and co-founders after a client request, the product grew to $12M+ in funding, 2,000 customers in 40 countries, 50 employees, and multiple seven-figure ARR by focusing on the underserved nonprofit market, transitioning from product-led to sales-driven growth, and building proprietary features like Spotlight video conferencing and calendar-of-record functionality.

Mode is a collaborative analytics and data science platform founded in 2013 by Ben Stancil, Derek, and Josh, all first-time founders who previously worked together at Yammer. The company grew from an internal tool used at Yammer into an eight-figure SaaS business with 150-200 employees serving enterprise customers like Anheuser-Busch, Bloomberg, DoorDash, and Zillow. They acquired early customers through content marketing focused on entertaining data-driven storytelling, product launch momentum, and their existing network in the analytics community.

Intro Hive is an AI-powered SaaS platform founded in 2011 by Jodi Glidden and Stuart that helps enterprises improve sales by automating CRM data capture, building accurate relationship graphs, and providing sales intelligence. After struggling for 3-4 years to solve the data quality problem (achieving 90% accuracy), the company shifted from inbound marketing (which yielded almost nothing) to a vertical-focused outbound strategy targeting accounting firms and global systems integrators. Today, Intro Hive serves hundreds of customers across 350-400 employees with tens of millions in revenue, aiming to hit $100 million ARR within 2-3 years, and has raised approximately $135 million in funding.

DecaLab is a SaaS acquisition and operating company founded by Raj Sheth that buys profitable B2B SaaS businesses in the $1-3M ARR range and scales them to $10M+. The company acquired Fly Data in 2020 for approximately $500K ARR, turned it around with product rewrites and growth initiatives, and sold it for a 3x return in about 13 months. Sheth's strategy focuses on operational improvements, SEO, onboarding, support, and outbound sales rather than creating products from scratch.

Crepling is a no-code e-commerce platform founded by brothers Liam (21) and Travis (18) from Malta. After selling their own Shopify sneaker resale store and attempting to launch an agency, they discovered the real market need was for a centralized, integrated e-commerce platform. They bootstrapped to 500+ customers and $1B+ GMV across all six continents through word-of-mouth and agency partnerships, recently raising a seed round from Jason Calacanis' Launch Accelerator.

Iris Shure founded Oribi, an AI-based web analytics tool built on a no-code data collection platform that helps marketers make data-driven decisions without requiring developers. After spending a year researching the market and building an initial Facebook Analytics product that gained early traction (first customer in 30 minutes), she killed it per investor feedback and pivoted to the larger vision. The company grew from 2 people to 60+ employees, thousands of customers, and $28M in funding by focusing on paid acquisition via Facebook and YouTube ads and optimizing pricing to $500+/month.

UserFlow is a no-code SaaS platform for building in-app onboarding guides and product tours, co-founded by Espen Fries Jensen and Sebastian. Started in 2018 (initially as Studio One, a video platform), it pivoted to interactive in-app guidance in 2019. With just two founders and a bootstrap approach (no VC funding), the company has grown to nearly $1M ARR by focusing on exceptional UX, product-led growth, and word-of-mouth marketing.

Live Help Now is an omnichannel customer support platform founded by Michael Kansky in 2005 as a side project extracted from his dating website's chat feature. After 4 years of hobby development, Michael monetized in 2009 by converting to a freemium model, immediately converting about one-third of his 800 users to paid plans and generating $10,000 MRR. The company grew to $3M ARR by 2017 primarily through organic tactics (review directories, SEO, word-of-mouth) but hit a growth plateau from 2017-2021 due to Michael's tendency to micromanage and split focus across multiple ventures, forcing him to finally hire a CEO and build a proper organizational structure.

Atrium is a sales management SaaS platform that helps sales managers and leaders use data-driven analytics to improve team performance. Founded by Pete Kazanji in 2016 after his experience at Monster Worldwide, the product instruments key sales KPIs (win rates, pipeline, customer-facing meetings, etc.) and uses statistical anomaly detection to surface actionable insights to non-technical sales managers. Pete pioneered the product through founder-led selling starting in 2018, acquiring a dozen customers before hiring his first sales rep in 2019.

Fat Merchant is a payment technology platform founded by Sunira Madhani in 2013 that enables businesses to accept payments across multiple channels (online, in-person, invoicing) through a unified platform with transparent, subscription-based pricing. Starting with $16k MRR from white-labeled solution customers and growing to $25M+ ARR, Fat Merchant scaled through an inbound digital marketing engine and later expanded via OmniConnect API for software partners. The company has raised over $100M in venture capital and processes $5B+ annually across 7,000+ customers.

DocSend is a horizontal SaaS platform that lets users securely share documents with real-time control and analytics instead of using email attachments. Founded by Russ Hedlstone and co-founders Dave and Tony, the company grew from free to $10/month pricing in 2016, experimented unsuccessfully with enterprise outbound sales (2016-2018), then pivoted back to self-serve with repositioned pricing and messaging—converting at higher rates as they increased prices. Today DocSend has 15,000+ customers, 55 employees, $15M+ raised, and is growing 75-80% year-over-year, powered primarily by word-of-mouth and organic/SEO channels.

InsureMe is a SaaS platform founded by 25-year-old Sunny Patel in 2016 that helps insurance carriers automate sales, claims, and customer service through an AI-driven assistant named Violet. Starting as a B2C comparison site, Patel pivoted to B2B after realizing the crowded consumer market required massive funding; he discovered carriers wanted to license the technology directly. The company has raised $1.1M in outside capital, operates with 12 employees from Phoenix, Arizona, and counts Fortune 100 carriers among its customers, with typical contract values ranging from $100K-$250K ARR and sales cycles of 6-8 months.

PatSnap is a connected innovation intelligence platform founded by Jeffrey Tiong in 2007 to help R&D teams and IP professionals identify technological opportunities. Tiong bootstrapped initial development with a $40,000 university startup grant and spent 2-3 years building the product while taking on consulting work to fund operations. The company now has 8,000 customers, 800 employees, and has raised over $51 million in funding, serving major clients like Disney, Tesla, and NASA.

Quiller, founded in 2014 by Dylan and Mark Tanner, helps sales and marketing teams create beautiful web-based proposals, quotes, and presentations as an alternative to PDFs and PowerPoints. Starting from Dylan's personal frustration with proposal creation at his micro agency, they grew to 3,000 customers and 45 employees through a freemium model, viral loops, and eventually moving upmarket to target larger sales and marketing teams. The company has raised $7.5 million and learned valuable lessons about freemium's tradeoffs and the importance of focusing on the right customer segment.

Salesflare is a sales CRM built by Yaroon Cortout and co-founder Michael Farmer that automates data capture from emails, meetings, and other sources, eliminating manual CRM updates. Starting from Yaroon's own pain point using Salesforce at a marketing agency, the product evolved from a Salesforce integration play into a standalone CRM for small B2B companies, particularly marketing and software development agencies. Through 2+ years of manual sales, PR efforts, a Product Hunt launch (200-300 trials, #1 CRM ranking), and a massive AppSumo campaign (6,000 signups in 3 weeks), the company has grown to serve over 2,000 customers and raised over $1 million.