
How to Win podcast with Peep Laja
Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories. No fluff. No filler. Just strategies and tactics from founders, executives, and marketers. Learn about building moats, growing audiences, scaling businesses, and differentiating from the competition. New guests every week. Hosted by Peep Laja, founder at Wynter, Speero, CXL.
Latest episodes

Feb 5, 2024 • 25min
Building a $180M PR Powerhouse with MuckRack's Gregory Galant
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] "Time to first million in revenue?"[00:05:51] "Early days buyer understanding?"[00:07:12] "Shift to sales-led approach?"[00:09:36] "Product and sales balance for growth?"[00:10:12] "Changes post-$10 million revenue?"[00:13:48] "Market size doubt at $10 million?"[00:18:09] "Reasons for outlasting competitors?"[00:20:24] "Top advice for B2B founders?"Mentioned:Gregory GalantMuck RackGregory Galant's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL

Jan 29, 2024 • 26min
Disrupting the B2B Marketplace -- with TrustRadius's Vinay Bhagat
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 Points:[00:02:30] - Inspiration behind your business model?[00:03:15] - Tackling initial cold start problem?[00:04:00] - Scaling outreach effectively?[00:05:15] - Competitive landscape at inception?[00:08:45] - Monetization through content syndication?[00:10:00] - No initial go-to-market strategy?[00:13:30] - Differentiation strategy in sales?[00:14:15] - Building a differentiated audience?[00:15:00] - Creating a buyer-centric platform?[00:18:00] - Strategy for targeting large tech companies?[00:18:45] - Focus on thought leadership and content?[00:19:45] - Advice for B2B founders?[00:20:15] - Balancing bootstrap with funding?[00:24:30] - TrustRadius's keys to winning?Mentioned:Vinay BhagatTrustRadius.comVinay Bhagat's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL

Jan 22, 2024 • 20min
The Differentiation Advantage - with Retention.com's Adam Robinson
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 growth and market penetration.Key Points:[01:48] - What was your first market product?[02:51] - How did it become a standalone product?[04:12] - Who's the primary buyer for this?[07:30] - Post-revenue, how did strategy evolve?[15:00] - How did you achieve business differentiation?[16:48] - Top three advice for B2B founders?[18:45] - What's behind Retention.com's winning strategy?Mentioned:Adam RobinsonRetention.comAdam Robinson's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL

Jan 8, 2024 • 27min
Finding Your Focus - with Blackthorn's Chris Federspiel
Chris Federspiel, CEO of Blackthorn.io, discusses the company's strategic growth in the Salesforce ecosystem and the role of customer feedback. Topics include go-to-market strategies, target customers, effective acquisition channels, and the importance of focus and industry expertise. They also touch on challenges in product development, shifting market focus, and working with partners for customer acquisition.

Dec 18, 2023 • 23min
Finding Your Ideal Customer Profile - with Keap's Clate Mask
Clate Mask, Co-founder and CEO of Keap, discusses finding the right customers, combining software with services, and evolving marketing. Highlights include building products based on business needs, serving small businesses dealing with chaos, and embracing partners for growth.

Dec 11, 2023 • 24min
Moving Upmarket for Growth - with Process Street's Vinay Patankar
Vinay Patankar, Founder and CEO of Process Street, discusses how they identified market needs, monetization strategies, transitioning to larger customers, revenue from inbound channels, differentiation amid competition, and advises founders on product and go-to-market strategies.

Dec 4, 2023 • 25min
Building a $15M+ Community - with Pavilion's Sam Jacobs
Entrepreneur Sam Jacobs, who built a $15 million community learning business, discusses leveraging LinkedIn for organic growth, creating sub-communities, and mistakes made after raising VC money. Key moments: Describing the company, issues with e-learning, cutting back, growing communities, advice for founders, and lessons learned.

Nov 27, 2023 • 18min
Bootstrapped to IPO - with Backblaze's Gleb Budman
Guest Gleb Budman, co-founder and CEO of Backblaze, discusses bootstrapping, serving mid-market customers, building their own platform, and the advantages of startups. They also talk about building an affordable storage infrastructure and learning from mistakes.

13 snips
Nov 20, 2023 • 23min
Raising Prices 50X - with indinero's Jess Mah
Jess Mah, Co-founder of indinero, discusses pivoting to a new customer segment, observing customer use to identify product issues, customizing marketing for each vertical, and replacing herself as CEO with an experienced leader.

Nov 15, 2023 • 22min
Getting the Timing Right - with Jellyfish's Andrew Lau
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 selling4:12 - Seeing massive growth after increasing COVID demand6:33 - Focusing on customer needs over competitors8:46 - Timing is everything - being patient10:58 - Staying focused on your team and customers12:33 - Acknowledging timing and people are key combinations14:52 - Funding marketing appropriately at different times22:41 - Timing is everything as operator, people are everything as investorMentioned:JellyfishAndrew LauMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL