How to Win podcast with Peep Laja Peep Laja

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 frustration03:00 Deciding not to monetize for 2 years to optimize fundraising06:15 Recognizing larger customers have higher retention and expansion07:00 Transitioning from SMB to mid-market and enterprise14:30 Having over 50% of revenue from inbound channels15:00 Needing specialized use cases to differentiate amid competition19:00 Advising founders to get very clear on product and go-to-market strategy
Mentioned:
Process Streethttps://www.process.st/
Vinay Patankar's Linkedinhttps://www.linkedin.com/in/vinaypatankar
Vinay Patankar on Xhttps://twitter.com/vinayp10?lang=en
My Links:
Twitter
LinkedIn
Website
Wynter
Speero
CXL

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 does06:20 - Describing the issues with e-learning11:30 - Issues with raising money 14:20 - Cutting back17:40 - Explaining how to grow communities22:30 - Advice for founders24:30 - Lessons learned
Mentioned:Pavilion
Sam Jacobs's LinkedInSam Jacobs's X
My Links:
X
LinkedIn
Website
Wynter
Speero
CXL

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-market02:15 Low pricing from efficient infrastructure07:45 Content and community marketing11:30 Bootstrapping forced efficiency13:20 Building own platform from bootstrapping16:15 Staying power and not getting ahead

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 more03:00 Combining QuickBooks, Mint.com and luxury concierge service04:15 Seeing product issues by observing customers use it08:00 Focusing on customer health and early churn indicators10:30 Customizing marketing and sales for each vertical16:15 Replacing yourself earlier as CEO with a more experienced leader
Mentioned:
LinkedIn
Twitter
indineroMahway
My Links:
Twitter
LinkedIn
Website
Wynter
Speero
CXL

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 - Timing is everything - being patient
10:58 - Staying focused on your team and customers
12:33 - Acknowledging timing and people are key combinations
14:52 - Funding marketing appropriately at different times
22:41 - Timing is everything as operator, people are everything as investor
Mentioned:
JellyfishAndrew Lau
My Links:
Twitter
LinkedIn
Website
Wynter
Speero
CXL

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 product-market fit
01:30 - First customer paying $50k, taking 3 months to get second
02:15 - Becoming workflow company based on customer feedback
03:00 - Enabling workflows with routing, notifications, messaging
04:15 - Going sales-led to getting feedback and sales quickly
05:00 - Moving upmarket for better economics
06:30 - Creating more value like selling furniture over lumber
07:30 - Getting Salesforce access to enabling workflows
09:00 - Pushing workflow steps to driving success
12:00 - Workflow products having better retention
13:30 - Hitting $1M revenue in 12-18 months
14:15 - Clipboard Health pivoting successfully
16:00 - Testing crazy versions when growth stalling
19:00 - Appearing bigger through LinkedIn, ads, case studies
22:15 - Focusing on use case despite competitors
23:45 - Building moat with brand recognition and revenue impact
25:15 - Saying no to unfit customers

Mentioned:
Christian Kletzl's LinkedInUserGems

My Links:
Twitter
LinkedIn
Website
Wynter
Speero
CXL