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:

1. [00:04:21] "Time to first million in revenue?"
2. [00:05:51] "Early days buyer understanding?"
3. [00:07:12] "Shift to sales-led approach?"
4. [00:09:36] "Product and sales balance for growth?"
5. [00:10:12] "Changes post-$10 million revenue?"
6. [00:13:48] "Market size doubt at $10 million?"
7. [00:18:09] "Reasons for outlasting competitors?"
8. [00:20:24] "Top advice for B2B founders?"

Mentioned:

Gregory Galant

Muck Rack
Gregory Galant's X

My Links:

Twitter / X

LinkedIn

Website

Wynter

Speero

CXL

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 Bhagat

TrustRadius.com
Vinay Bhagat's X

My Links:

Twitter / X

LinkedIn

Website

Wynter

Speero

CXL

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 Robinson

Retention.com
Adam Robinson's X

My Links:

Twitter / X

LinkedIn

Website

Wynter

Speero

CXL

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.

Key Points:

00:00:16 How did Blackthorn achieve its growth?
00:01:30 How long to build first product?
00:03:36 Time to hit 1 million ARR?
00:04:21 Target customers for your products?
00:06:09 Explain go-to-market strategy?
00:08:18 Go-to-market for growth acceleration?
00:09:54 Current product lineup?
00:14:10 Target customer segment evolution?
00:16:09 Effective customer acquisition channels?
00:17:42 Monitoring competition?
00:19:12 Unsuccessful strategic bets?
00:21:45 Importance of company focus?
00:22:12 What set Blackthorn apart from others?
00:24:00 Top advice for B2B founders?
00:25:57 How did Blackthorn win?

Mentioned:

Chris Federspiel

Blackthorn.io
Chris Federspiel's X

My Links:

Twitter / X

LinkedIn

Website

Wynter

Speero

CXL

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 marketing automation to full business automation
07:15 Renaming the company to reflect simplicity and ease of use
09:45 Sticking to core small business customers amid pressure
13:00 Combining software, services, and strategy for customer success
22:30 Embracing partners and gradual upmarket moves for growth

Mentioned:

Clate Mask's Linkedin
Clate Mask's X
Keap

My Links:

Twitter

LinkedIn

Website

Wynter

Speero

CXL

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 fundraising
06:15 Recognizing larger customers have higher retention and expansion
07:00 Transitioning from SMB to mid-market and enterprise
14:30 Having over 50% of revenue from inbound channels
15:00 Needing specialized use cases to differentiate amid competition
19:00 Advising founders to get very clear on product and go-to-market strategy

Mentioned:

Process Street
https://www.process.st/

Vinay Patankar's Linkedin
https://www.linkedin.com/in/vinaypatankar

Vinay Patankar on X
https://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 does
06:20 - Describing the issues with e-learning
11:30 - Issues with raising money
14:20 - Cutting back
17:40 - Explaining how to grow communities
22:30 - Advice for founders
24:30 - Lessons learned

Mentioned:
Pavilion

Sam Jacobs's LinkedIn
Sam 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-market
02:15 Low pricing from efficient infrastructure
07:45 Content and community marketing
11:30 Bootstrapping forced efficiency
13:20 Building own platform from bootstrapping
16:15 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 more
03:00 Combining QuickBooks, Mint.com and luxury concierge service
04:15 Seeing product issues by observing customers use it
08:00 Focusing on customer health and early churn indicators
10:30 Customizing marketing and sales for each vertical
16:15 Replacing yourself earlier as CEO with a more experienced leader

Mentioned:

LinkedIn

Twitter

indinero
Mahway

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:

Jellyfish
Andrew Lau

My Links:

Twitter

LinkedIn

Website

Wynter

Speero

CXL