How to Win podcast with Peep Laja

In this episode, Peep Laja is joined by Kathleen Booth and Dave Gerhardt to unpack the real buying behavior behind B2B SaaS in 2025. They break down the power of dark social, peer communities, and brand storytelling in an era where Google is no longer the first stop. Learn how to win trust, get talked about, and drive growth—without a single paid ad. Chapters: [00:00:00] Buyers No Longer Start on...

Peep Laja dives into why speed is a critical and often underrated competitive advantage in today's fast-paced business world. Learn how to make swift decisions, conduct rapid experiments, ship products and campaigns quickly, and gather market feedback efficiently. Drawing from historical military strategies and modern business practices, Peep explains how speed can help you stay ahead of the compe...

In this episode, Peep Laja emphasizes the importance of deeply understanding your target market and ideal customer profile (ICP) to drive growth in B2B SaaS. He advocates for ongoing research to inform effective messaging, breaks down the key components of high-converting copy, and shares how tools like Wynter enable teams to get fast feedback and align around the ICP. By implementing these strate...

In this episode, Peep dives into why niching down is the key to success for early-stage B2B SaaS companies. He explains how focusing on solving a specific problem for a targeted market, rather than competing directly with industry giants, allows startups to gain traction and dominate their niche. Peep emphasizes that niching down isn't about limiting your dreams, but rather a proven strategy to br...

In this episode, Peep Laja explores the scientific laws of marketing, focusing on building mental and physical availability for brands. Drawing from the works of Professor Byron Sharpe and the Ehrenberg Bass Institute, Laja emphasizes the importance of being top of mind and easily found when potential customers are ready to make a purchase. The episode features insights from marketing experts who...

This episode explores the critical factors that define market leadership, from being first in a category to leveraging innovation and strategic marketing. Hear from experts like David Aaker, Mark Ritson, and Byron Sharp on how top brands maintain dominance and why small brands face uphill battles. Discover actionable insights on standing out, staying top of mind, and converting prospects into loya...

In this new style of "How To Win", Peep Laja discusses the importance of differentiation in today's highly competitive B2B SaaS market. He explores various strategies for standing out, such as focusing on brand, taking a polarizing stance, being radically transparent, and leveraging personal brands. Laja emphasizes that differentiation is a CEO-level problem and that companies must build their vis...

This week on How To Win: Noah Kagan of AppSumo , a platform for digital marketplace deals focusing on software aimed at entrepreneurs and small businesses. They have bootstrapped to over $80 million in revenue. You’ll hear insights on scaling business by focusing on what works, the importance of staying true to your core values, and the strategy behind AppSumo 's success. Discover how AppSumo thri...

This week on How To Win: Bernat Farrero of Factorial HR , sharing insights on revolutionizing HR for SMBs. You’ll hear about the importance of simplifying complex HR processes for small and medium businesses, Factorial HR 's strategic approach to scaling internationally while addressing localized needs, and how they navigated the challenges of rapid growth and product development to meet the diver...

This week on How To Win: Todd Olson of Pendo , revealing the secrets behind building a product-led growth company. You’ll hear how Pendo 's focus on product experience revolutionized customer interaction, the importance of integrating customer feedback into product development for sustained growth, and the strategic approach to scaling a software company beyond traditional boundaries. Key Points:...

This week on How To Win: Gregory Galant of Muck Rack , discusses the journey of transforming a podcasting venture into a leading software solution for public relations professionals. You’ll hear insights on the importance of building strong journalist relationships, the strategic pivot from service to software, and the value of slow, deliberate growth in the tech industry. Key Points: [00:04:21] "...

This week on How To Win: Vinay Bhagat of TrustRadius , revolutionizing B2B software buying with in-depth user reviews. You’ll hear how TrustRadius overcame the challenge of creating a trusted review platform in a saturated market, the strategic decisions that led to successful monetization, and the importance of focusing on quality over quantity to cater to both software vendors and buyers. Key Po...

This week on How To Win: Adam Robinson of Retention.com , an innovative leader in the email marketing space. You’ll hear about the journey of identifying a market gap and creating a differentiated product in a competitive environment, the importance of strategic focus on a specific target market, particularly in e-commerce, and the implementation of focused go-to-market strategies for sustained gr...

This week on How To Win: Chris Federspiel of Blackthorn.io , a company specializing in Salesforce integration and application development. You’ll hear about Blackthorn's strategic approach to the Salesforce ecosystem, the critical role of customer feedback in shaping their product development, and the journey of focusing their offerings to achieve significant growth in the competitive SaaS market....

This week on How To Win: Clate Mask of Keap, marketing automation and CRM platform for small businesses. You'll hear how Keap found the right customers, why they combined software with services, and how Keap evolved its marketing over time. Key Points: 01:15 Building the initial product based on own business needs 03:00 Pivoting to serve small businesses dealing with chaos 04:30 Evolving from just...

This week on How To Win: Vinay Patankar of Process Street, a workflow management software company. You'll hear why they didn't monetize for the first 2 years, how going upmarket increased retention and revenue, and why they focused the product on specific use cases. Key Points: 01:15 Identifying market need from personal frustration 03:00 Deciding not to monetize for 2 years to optimize fundraisin...

This week on How To Win: Sam Jacobs of Pavilion, who built a $15 million community learning business from scratch. You’ll hear how he leveraged LinkedIn for organic growth, the importance of creating sub-communities, and key mistakes he made after raising VC money that took the focus away from his core customers. Key moments: 00:50 - Describing what the company does 06:20 - Describing the issues w...

This week on How To Win: Gleb Budman of Backblaze, which offers affordable, easy cloud storage. You’ll hear how bootstrapping forced them to make efficient decisions, how focusing on underserved mid-market customers helped them compete with Amazon, and how building their own platform gave them a structural advantage. Timestamps: 01:45 Focusing on underserved mid-market 02:15 Low pricing from effic...

This week on How To Win: Jess Mah of indinero, a fintech company providing automated bookkeeping and accounting services. You'll hear how she focused on high-paying niche verticals, pivoted to find product-market fit, and how she brought in an experienced CEO. Key Points: 01:45 Pivoting to a new customer segment willing to pay more 03:00 Combining QuickBooks, Mint.com and luxury concierge service...

This week on How To Win: Andrew Lau of Jellyfish, the engineering management platform. You'll hear how they validated the problem space, figured out product-market fit, and used founder-led sales to generate traction. Key Points: 2:03 - Getting first revenue with founder-led selling 4:12 - Seeing massive growth after increasing COVID demand 6:33 - Focusing on customer needs over competitors 8:46 -...

Summary This week on How To Win: Christian Kletzl of UserGems, champion tracking software for sales. You'll hear the process they went through to find the product their clients were willing to pay for, how they make themselves appear bigger than they are, and more. Key Points 00:30 - Appearing larger by using ads, content, LinkedIn, conferences 01:00 - Pivoting multiple times before finding produc...

This week on How To Win: Livestorm's Gilles Bertaux, a meeting and webinar platform. You'll hear how Livestorm succeeded despite many well-known competitors. How they got their first customers. And how they grew past $10 million in revenue. Key Points 1:00 - How Gilles got the idea for Livestorm and validated it with customers 2:00 - Getting the first set of customers 3:15 - Reaching $1 million AR...

This week on How To Win: Guy Cohen, CEO of Wonder an on-demand secondary research platform. They built the company to 8M in revenue, realized their ICP was wrong, tore it down and rebuilt again. That's what we break down in this episode. Key Points: 00:02:29 Failed many times, learned hard lessons, narrowed target. 00:04:28 Innovative marketing approach convinces lighthouse customers. 00:09:12 Can...

Summary   This week on How To Win: Spencer Fry of Podia, the all-in-one platform for publishing, promoting, and selling content online. You'll learn how Podia succeeded in the face of heavy competition. Why the benefits of having multiple products outweigh the downsides for Podia. How Podia's long-term investment affects everything from product creation to marketing decisions. And more. Key Points...

Summary This week on How To Win: Andrew Gazdecki of Acquire.com, the startup acquisition marketplace. You'll hear: How Andrew lands Times Square advertising to promote startups on his platform. How he went from doing everything himself to quickly assembling a team to speed up his company's growth rate. How he discovered a big opportunity to create a new company in the mergers and acquisitions mark...