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Unusual insights from our team and portfolio

Eynat Guez on Papaya Global’s journey to PMF
September 10, 2025
Eynat Guez on Papaya Global’s journey to PMF
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Why we’re leading Helios $4m Seed Round
July 11, 2025
Why we’re leading Helios $4m Seed Round
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The beginning is beautiful – don’t rush to prove something
May 29, 2025
The beginning is beautiful – don’t rush to prove something
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Why we’re doubling down on Chalk
May 28, 2025
Why we’re doubling down on Chalk
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Unusual Ventures welcomes Brett Teele as Chief Financial Officer
May 12, 2025
Unusual Ventures welcomes Brett Teele as Chief Financial Officer
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Crossing the enterprise chasm and into the mainstream: Lessons from Geoffrey Moore
May 07, 2025
Crossing the enterprise chasm and into the mainstream: Lessons from Geoffrey Moore
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A warm welcome to Jill Puente, our new Chief Marketing Officer!
May 02, 2025
A warm welcome to Jill Puente, our new Chief Marketing Officer!
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Our Series B investment in global payments innovator Navro
April 29, 2025
Our Series B investment in global payments innovator Navro
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Congratulations to Relyance AI on the launch of Data Journeys!
April 23, 2025
Congratulations to Relyance AI on the launch of Data Journeys!
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Jyoti Bansal on how Traceable found product-market fit
April 08, 2025
Jyoti Bansal on how Traceable found product-market fit
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How startups can benefit from the Innovator’s Dilemma: 3 lessons from Clay Christensen
March 27, 2025
How startups can benefit from the Innovator’s Dilemma: 3 lessons from Clay Christensen
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Pattern Breakers can reshape the future: 4 insights for startup founders
February 28, 2025
Pattern Breakers can reshape the future: 4 insights for startup founders
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It’s not about perfection: Your Annual Operating Plan is a learning framework
February 26, 2025
It’s not about perfection: Your Annual Operating Plan is a learning framework
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How Paxton built its legal AI assistant: An Unusual Academy case study
February 20, 2025
How Paxton built its legal AI assistant: An Unusual Academy case study
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Success is not a Zero-Sum Game: 5 Lessons from Adam Grant’s ‘Give and Take’
January 30, 2025
Success is not a Zero-Sum Game: 5 Lessons from Adam Grant’s ‘Give and Take’
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Why we’re leading Paxton’s $22 million Series A round
January 29, 2025
Why we’re leading Paxton’s $22 million Series A round
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5 Reasons Enterprise Buyers Will Invest in Your AI Solution
January 24, 2025
5 Reasons Enterprise Buyers Will Invest in Your AI Solution
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Why enterprise startup founders shouldn’t rush into hiring their first sales leader
January 08, 2025
Why enterprise startup founders shouldn’t rush into hiring their first sales leader
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Why we invested in GovSignals: the AI platform for Government Contracting
December 12, 2024
Why we invested in GovSignals: the AI platform for Government Contracting
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Ideas that are Made to Stick: 6 principles from Chip and Dan Heath
December 10, 2024
Ideas that are Made to Stick: 6 principles from Chip and Dan Heath
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Building an AI Startup? 5 Reflections on the two-year Anniversary of GPT-3
November 21, 2024
Building an AI Startup? 5 Reflections on the two-year Anniversary of GPT-3
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How to hire (and lead) people who think like owners
November 14, 2024
How to hire (and lead) people who think like owners
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Goldcast CEO Palash Soni on AI-powered Enterprise Video Campaigns
November 12, 2024
Goldcast CEO Palash Soni on AI-powered Enterprise Video Campaigns
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Is your startup idea good? 5 takeaways from Rob Fitzpatrick’s Mom Test
October 31, 2024
Is your startup idea good? 5 takeaways from Rob Fitzpatrick’s Mom Test
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Relyance AI’s series B — Helping Enterprises Achieve Trust with Confidence
October 10, 2024
Relyance AI’s series B — Helping Enterprises Achieve Trust with Confidence
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Why we invested in AirOps
October 03, 2024
Why we invested in AirOps
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Samantha Mckenna on why solving customer problems is the best sales strategy
September 26, 2024
Samantha Mckenna on why solving customer problems is the best sales strategy
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Small changes can be transformative: 3 takeaways from Atomic Habits by James Clear
September 18, 2024
Small changes can be transformative: 3 takeaways from Atomic Habits by James Clear
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Software startups should embrace unreasonable hospitality: 3 takeaways from Relyance AI’s Abhi Sharma
September 12, 2024
Software startups should embrace unreasonable hospitality: 3 takeaways from Relyance AI’s Abhi Sharma
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Connectly’s Series B — Building the future of AI-powered conversational commerce
September 10, 2024
Connectly’s Series B — Building the future of AI-powered conversational commerce
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Unreasonable Hospitality is good business: 5 lessons from Will Guidara
July 25, 2024
Unreasonable Hospitality is good business: 5 lessons from Will Guidara
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Want to understand the elements of a strong business? Think of it as a 3-layer cake!
July 10, 2024
Want to understand the elements of a strong business? Think of it as a 3-layer cake!
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Are you building a visionary company? What we learned from ‘Built to Last’ by Collins and Porras
June 26, 2024
Are you building a visionary company? What we learned from ‘Built to Last’ by Collins and Porras
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Why we’re leading EnFi’s $7.5m seed round
June 20, 2024
Why we’re leading EnFi’s $7.5m seed round
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Starting an M&A process? 10 tips to increase your situational awareness
June 18, 2024
Starting an M&A process? 10 tips to increase your situational awareness
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Why we were the first investors in Tobiko Data
June 05, 2024
Why we were the first investors in Tobiko Data
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Don’t Settle for “good”: 3 Lessons from ‘Good to Great’ by Jim Collins
May 30, 2024
Don’t Settle for “good”: 3 Lessons from ‘Good to Great’ by Jim Collins
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Selling AI to Big Enterprises: A Conversation with Joel Hron at Thomson Reuters
April 23, 2024
Selling AI to Big Enterprises: A Conversation with Joel Hron at Thomson Reuters
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From sales skeptic to expert: 4 steps for new founders
April 04, 2024
From sales skeptic to expert: 4 steps for new founders
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Why we’re leading Theia Insights’ $6.5m seed round
March 06, 2024
Why we’re leading Theia Insights’ $6.5m seed round
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Why values-driven leadership matters: 5 takeaways from Hometap’s Jeff Glass
January 31, 2024
Why values-driven leadership matters: 5 takeaways from Hometap’s Jeff Glass
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Why we co-led Chalk’s seed round
December 12, 2023
Why we co-led Chalk’s seed round
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4 areas Gen AI will impact the knowledge worker in asset and wealth management
December 05, 2023
4 areas Gen AI will impact the knowledge worker in asset and wealth management
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How do you Navigate AI Security in an Evolving Landscape?
November 29, 2023
How do you Navigate AI Security in an Evolving Landscape?
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Founders have 30 minutes to nail their pitch. Here’s how to ace the pace.
September 29, 2023
Founders have 30 minutes to nail their pitch. Here’s how to ace the pace.
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CO2 AI: The future of sustainability management software
September 13, 2023
CO2 AI: The future of sustainability management software
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LLMs in security: What are the opportunities for startups?
September 06, 2023
LLMs in security: What are the opportunities for startups?
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Why we’re leading Portrait Analytics’ $7m Seed round
July 20, 2023
Why we’re leading Portrait Analytics’ $7m Seed round
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Whose responsibility is responsible AI?
June 28, 2023
Whose responsibility is responsible AI?
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The race for identity verification and onboarding is on! How will Generative AI make an impact?
June 15, 2023
The race for identity verification and onboarding is on! How will Generative AI make an impact?
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How to find product market fit: the counterintuitive secrets
June 08, 2023
How to find product market fit: the counterintuitive secrets
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How is AI Changing the way Software is Developed?
June 06, 2023
How is AI Changing the way Software is Developed?
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How good is your language model? Nobody knows yet
May 26, 2023
How good is your language model? Nobody knows yet
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The tug-of-war between lighthouse customers and your product roadmap
May 19, 2023
The tug-of-war between lighthouse customers and your product roadmap
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What will the security stack for generative AI applications look like?
May 16, 2023
What will the security stack for generative AI applications look like?
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Apply for Unusual’s Summer AI studio
May 03, 2023
Apply for Unusual’s Summer AI studio
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Why we’re leading Vizcom AI’s $5M Seed round
May 02, 2023
Why we’re leading Vizcom AI’s $5M Seed round
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Celebrating 5 years of Unusual Ventures
April 26, 2023
Celebrating 5 years of Unusual Ventures
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Why we led Qdrant’s $7.5M Seed round
April 19, 2023
Why we led Qdrant’s $7.5M Seed round
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Investing in Roboto: copilot for robotics data
April 06, 2023
Investing in Roboto: copilot for robotics data
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This is what AI builders should know about data protection and privacy
March 29, 2023
This is what AI builders should know about data protection and privacy
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Unlocking commerce across borders: Why we’re leading Navro’s $18.3M Series A
March 29, 2023
Unlocking commerce across borders: Why we’re leading Navro’s $18.3M Series A
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DataStax CEO Chet Kapoor on mastering the art of the no-look pass
March 02, 2023
DataStax CEO Chet Kapoor on mastering the art of the no-look pass
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Here’s why founders should do customer discovery
March 01, 2023
Here’s why founders should do customer discovery
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With $53M raise, Descope is poised to lead the passwordless future for developers
February 16, 2023
With $53M raise, Descope is poised to lead the passwordless future for developers
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How Harness found product-market fit: Jyoti Bansal on striking gold with customer discovery
February 13, 2023
How Harness found product-market fit: Jyoti Bansal on striking gold with customer discovery
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Generative AI is blowing up. What does this mean for cybersecurity?
January 31, 2023
Generative AI is blowing up. What does this mean for cybersecurity?
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4 fintech and SaaS areas primed for growth in 2023 despite tough macroeconomics
January 11, 2023
4 fintech and SaaS areas primed for growth in 2023 despite tough macroeconomics
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Can’t find a business mentor? Try the ‘Rule of 10’ instead
November 23, 2022
Can’t find a business mentor? Try the ‘Rule of 10’ instead
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CEO Rapidfire: Learnings from Ali Ghodsi, co-founder & CEO Of Databricks, on the journey to $1B+ ARR
November 17, 2022
CEO Rapidfire: Learnings from Ali Ghodsi, co-founder & CEO Of Databricks, on the journey to $1B+ ARR
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Lessons from Flywire’s journey to multibillion–dollar valuation
October 26, 2022
Lessons from Flywire’s journey to multibillion–dollar valuation
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How Vivun raised a Seed round
October 21, 2022
How Vivun raised a Seed round
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Andy Rachleff on coining the term product-market fit
October 10, 2022
Andy Rachleff on coining the term product-market fit
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Core fintech themes and advice for founders in today’s market
September 22, 2022
Core fintech themes and advice for founders in today’s market
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Investing in Dopt
September 21, 2022
Investing in Dopt
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13 of The Most Inspiring Books for Startup Founders
September 08, 2022
13 of The Most Inspiring Books for Startup Founders
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Where’s the Series A market now?
August 16, 2022
Where’s the Series A market now?
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The benefits of being Unusual: Why I joined Unusual Ventures
July 27, 2022
The benefits of being Unusual: Why I joined Unusual Ventures
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Introducing Unusual Ventures Boston
June 29, 2022
Introducing Unusual Ventures Boston
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Reimagining loyalty: Our investment in TYB
June 02, 2022
Reimagining loyalty: Our investment in TYB
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Heartex’s $25M Series A
May 18, 2022
Heartex’s $25M Series A
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Announcing $485M Unusual Ventures Fund III
May 05, 2022
Announcing $485M Unusual Ventures Fund III
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Unlocking omnichannel: Our investment in Lucky
April 08, 2022
Unlocking omnichannel: Our investment in Lucky
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Loyalty 3.0:  Where consumers become owners
April 06, 2022
Loyalty 3.0: Where consumers become owners
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Unusual Insights for founders building a self-service motion
March 10, 2022
Unusual Insights for founders building a self-service motion
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What are the best tools for startup founders?
February 24, 2022
What are the best tools for startup founders?
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Reimagining B2B marketing with Goldcast
February 17, 2022
Reimagining B2B marketing with Goldcast
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Building momentum: why I have joined Unusual Ventures
January 19, 2022
Building momentum: why I have joined Unusual Ventures
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Rewriting the rules of retail: our investment in Purple Dot
January 04, 2022
Rewriting the rules of retail: our investment in Purple Dot
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Building and scaling a growth team — Key insights from Andy Johns’ new 20 Minute VC interview
November 17, 2021
Building and scaling a growth team — Key insights from Andy Johns’ new 20 Minute VC interview
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Unusual Founder’s Video Series: Fundraising at Series A and How to Choose an Investor
November 16, 2021
Unusual Founder’s Video Series: Fundraising at Series A and How to Choose an Investor
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Congratulating Sarah Leary on a founder’s milestone!
November 08, 2021
Congratulating Sarah Leary on a founder’s milestone!
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Operator insights: How to Pick the Right “0-1” Sales Role
October 20, 2021
Operator insights: How to Pick the Right “0-1” Sales Role
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Giving Data Privacy Professionals real-Time insights — our Seed and Series A in Relyance AI
September 15, 2021
Giving Data Privacy Professionals real-Time insights — our Seed and Series A in Relyance AI
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Ready to join an early-stage startup as their first sales lead?
September 08, 2021
Ready to join an early-stage startup as their first sales lead?
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How Carta won their first 100 customers
August 19, 2021
How Carta won their first 100 customers
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Robinhood’s IPO: Democratizing Finance for All
July 29, 2021
Robinhood’s IPO: Democratizing Finance for All
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Automating and Scaling Inside Sales Teams—Our Series A in Orum
July 27, 2021
Automating and Scaling Inside Sales Teams—Our Series A in Orum
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Styra’s Unusual Journey
July 22, 2021
Styra’s Unusual Journey
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Betting on Endgame
July 13, 2021
Betting on Endgame
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Traceable’s Unusual Journey
June 30, 2021
Traceable’s Unusual Journey
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Contra’s Unusual Journey
June 03, 2021
Contra’s Unusual Journey
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An Unusual Journey: Grateful After Three Years
May 20, 2021
An Unusual Journey: Grateful After Three Years
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Unusual Founder’s Video Series: The Guide to Fundraising
May 19, 2021
Unusual Founder’s Video Series: The Guide to Fundraising
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Unusual Participates in $12M Series A in BluBracket: Securing Code in a Software-Driven World
May 13, 2021
Unusual Participates in $12M Series A in BluBracket: Securing Code in a Software-Driven World
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Seed Stage Founders: The Current Market for Series A Financings
May 11, 2021
Seed Stage Founders: The Current Market for Series A Financings
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Alto—Raising the Bar for the Self-Directed IRA Industry
April 20, 2021
Alto—Raising the Bar for the Self-Directed IRA Industry
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Deep Collaboration in the Enterprise: Till Pieper, Max Andaker, and Jason Thomas, Co-Founders, CoScreen
April 15, 2021
Deep Collaboration in the Enterprise: Till Pieper, Max Andaker, and Jason Thomas, Co-Founders, CoScreen
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Sitting Down with Next Play Perspectives Podcast
March 31, 2021
Sitting Down with Next Play Perspectives Podcast
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Unleashing Deep Collaboration for Engineering Teams — Our Seed in CoScreen
March 25, 2021
Unleashing Deep Collaboration for Engineering Teams — Our Seed in CoScreen
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Introducing Unusual Spark — Our Pre-Seed Program to Support Founders from Day Zero
March 17, 2021
Introducing Unusual Spark — Our Pre-Seed Program to Support Founders from Day Zero
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Powering the Future of Independent Work — Our Series A in Contra
February 23, 2021
Powering the Future of Independent Work — Our Series A in Contra
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Five Emerging Trends in AI
February 11, 2021
Five Emerging Trends in AI
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Our Continued Partnership with Vivun
February 10, 2021
Our Continued Partnership with Vivun
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Three Common Pitfalls of AI Pitches
February 10, 2021
Three Common Pitfalls of AI Pitches
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Jyoti Bansal — An Inspiration for Us All
January 15, 2021
Jyoti Bansal — An Inspiration for Us All
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Unusual Roundtable Takeaways: Data Lineage and its Role in Data Unification
January 15, 2021
Unusual Roundtable Takeaways: Data Lineage and its Role in Data Unification
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Arrikto—Unlocking the Acceleration Potential of Machine Learning Ops in the Enterprise
November 16, 2020
Arrikto—Unlocking the Acceleration Potential of Machine Learning Ops in the Enterprise
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Unusual Tech: Workflow Orchestration White Paper
October 21, 2020
Unusual Tech: Workflow Orchestration White Paper
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Vivun—Empowering Presales Teams to be the Heroes of the Enterprise
October 14, 2020
Vivun—Empowering Presales Teams to be the Heroes of the Enterprise
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Making the Pivot: The Unusual Founder Workshop Series
July 28, 2020
Making the Pivot: The Unusual Founder Workshop Series
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Traceable—Protecting Cloud-Native Applications and APIs from Modern Cybersecurity Threats
July 14, 2020
Traceable—Protecting Cloud-Native Applications and APIs from Modern Cybersecurity Threats
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Presales Champions: Matt Darrow, Dominique Darrow, John Bruce, and Claire Bruce, Co-Founders, Vivun
May 19, 2020
Presales Champions: Matt Darrow, Dominique Darrow, John Bruce, and Claire Bruce, Co-Founders, Vivun
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Announcing the Unusual Guide for Raising Seed and Series A Capital
May 13, 2020
Announcing the Unusual Guide for Raising Seed and Series A Capital
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GitHub’s CTO Jason Warner on Managing Remote Teams
April 29, 2020
GitHub’s CTO Jason Warner on Managing Remote Teams
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Best Practices for Running Remote Teams
March 24, 2020
Best Practices for Running Remote Teams
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Ride Report — Bridging the Gap in Micromobility
March 12, 2020
Ride Report — Bridging the Gap in Micromobility
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Sales Connector: Jason Dorfman, Co-Founder and CEO, Orum
March 10, 2020
Sales Connector: Jason Dorfman, Co-Founder and CEO, Orum
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BluBracket — Securing Code in a Software-Driven World
February 19, 2020
BluBracket — Securing Code in a Software-Driven World
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Kloud.io — Democratizing Data Access for Financial Analysts
January 30, 2020
Kloud.io — Democratizing Data Access for Financial Analysts
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20 Minute VC: My ‘Unusual’ Conversation with Harry Stebbings
December 09, 2019
20 Minute VC: My ‘Unusual’ Conversation with Harry Stebbings
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Vivun — Unleashing the Power of Presales in the Enterprise
November 26, 2019
Vivun — Unleashing the Power of Presales in the Enterprise
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Banyan — Securing the Enterprise with Zero Trust Remote Access
November 22, 2019
Banyan — Securing the Enterprise with Zero Trust Remote Access
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Raising the Bar Even Higher for Seed Stage Founders
November 18, 2019
Raising the Bar Even Higher for Seed Stage Founders
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Styra — Expanding Open Source and Commercial Solutions for Kubernetes/Cloud-Native Security
November 12, 2019
Styra — Expanding Open Source and Commercial Solutions for Kubernetes/Cloud-Native Security
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Recruiting to Win at the Seed Stage
October 24, 2019
Recruiting to Win at the Seed Stage
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Shujinko — Simplifying Cloud Compliance
October 08, 2019
Shujinko — Simplifying Cloud Compliance
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Playing to Win: Aaron Hawkey and Robert Angarita, Co-Founders, BallerTV
September 05, 2019
Playing to Win: Aaron Hawkey and Robert Angarita, Co-Founders, BallerTV
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Splunk Acquires Omnition.io, Unusual’s First Investment
September 04, 2019
Splunk Acquires Omnition.io, Unusual’s First Investment
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Early Education Crusader: Chris Bennett, Co-Founder and CEO of Wonderschool
August 27, 2019
Early Education Crusader: Chris Bennett, Co-Founder and CEO of Wonderschool
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The Rage to Master: The One Unusual Thing All Entrepreneurs Must Have to Win
July 25, 2019
The Rage to Master: The One Unusual Thing All Entrepreneurs Must Have to Win
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Unusual Academy: Empowering Founders to Learn by Doing
June 03, 2019
Unusual Academy: Empowering Founders to Learn by Doing
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