Issac J Roth

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Pre-COVID SaaS startup investing had evolved into something of a numbers game; especially post Series A at the expansion capital stage. In the oft-cited T2D3 formula, companies that tripled ARR in consecutive years then had doubled or were on track to double thrice in a row were set for greatness. Later stage investors could almost “color by numbers” and plug in these formulae to predict success.

The COVID economic season has reset everyone’s plans and changed what investors are looking for. As a small firm we have invested just under $1B in enterprise SaaS companies at the early stages and helped 25 of them get over $10M in annual revenue, 15 of them over $30M, we are reflecting on the hard work it takes to get from the stage where we invest — a few initial customers — to being ready for expansion capital. …


As we’ve shifted to a largely virtual world over the past few months, online presentations have taken the spotlight as conferences and in-person meetings have been put on hold. What does this mean for online content creators? How has the pandemic changed the role of presentations?

We recently sat down with Beautiful.ai President/COO, Jason Lapp, to discuss a wide range of topics, from how AI is making presentations more efficient (and beautiful) to how they’re adapting to common work from home challenges.

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Tell us about Beautiful AI and what makes it unique compared to other presentation tools?

We’re solving a major pain point for anyone who creates presentations and slides. We’re democratizing design by making the product the designer so anyone can create great looking content. We’re transitioning the way people create, work and think when it comes to building presentations. …


The latest news, thought leadership, and insights from the innovative companies shaping their industries.

5 Employee Training Lessons Learned in One Year

Highspot highlights how they develop and inspire their most prized assets — their employees. One year ago they launched the GROW program for new employees with perfect timing as they’ve seen their headcount triple since the program began. The result? More engaged employees and a 139% increase in the number of reps hitting their quota. So what are key takeaways from lessons learned? Their Revenue Enablement Manager, Jessica Boyd, offers insights.

Tonal teams up with six-time IRONMAN World Champion Mark Allen Grip to get you triathlon…


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We continue our Shasta Ignite series exploring how companies can manage through crises and economic downturns by bringing together two experienced perspectives: Ravi Mohan, Partner at Shasta and a 25 year venture investor through multiple downturns, and serial entrepreneur Sunny Gupta, who is currently the CEO of Apptio.

Sunny brings a unique perspective to the conversation through his experience of founding Apptio in November 2007. …


By Kenn So

Having built multiple financial models for Shasta, I am ‘open sourcing’ a templatized version for SaaS startups replanning in this environment and the advisors helping them.

The tricky part about building a model is finding the right balance between detail for accuracy, simplicity for agility, and flexibility for scalability. This model has worked for me across those criteria, with a couple of notes and caveats:

  • as a Series A-focused fund, this model is geared towards companies with early revenue and without distinct sales motions for different customer segments
  • the model fits a sales-led business with annual contracts
  • the use of this model is for monthly operational & cash planning, not valuation — so not your annual investment banking model. …


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How can startups retain customers and plan for the future during these unprecedented times?

We brought together three experienced perspectives: Issac Roth, Partner at Shasta and creator of Red Hat OpenShift and StrongLoop, Ravi Mohan, Partner at Shasta and a 25 year venture investor through multiple downturns, and Michael Lock, Advisor at Shasta and co-founder of Google GSuite.

The webinar is a part of an ongoing series addressing challenges brought on by the severe demand shock that we’re facing.

In this session we focused on three key topics:

  • Managing customers and potentially higher churn rates
  • Predicting what churn is going to be for planning…


By: Michael Lock, Shasta Ventures

I was a sales leader in 2001 when the dot.com bubble burst and when the planes hit the towers. I was a sales leader when Lehman Brothers failed and we questioned the very foundations of our banking and capitalist systems. However, this downturn is different. It’s more sudden, more shocking, more lethal. That having been said, I think there is much for sales leaders to learn from 2001 and 2008.

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These are the seven most important lessons I learned from those downturns:

1. Customers first. Always.

My guess is that your forecast for gross retention and net retention was based on data for 2018 and 2019.

Times have changed.

You can’t take high renewal rates and robust upsells for granted anymore.You should go through your renewal list line by line, account by account, situation by situation and re-assess your assumptions. Look at the usage rate of your product in those customers and assess the financial health of the customer in a post COVID economy. …


How can startups navigate this unprecedented crisis?

During a recent virtual town hall, some of our most experienced partners and entrepreneurs shared their thoughts and lessons on leadership and resilience during challenging times, inspired by their own experiences maneuvering through 2001’s dot com bust and 2008’s Great Recession.

You can watch the recorded Zoom session here. Pro tip: you can watch id 1.5X or @x speed to save time. :-)

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Here are some quick highlights:

Ravi Mohan, Managing Director at Shasta, started off the session optimistically by pointing out that in previous down turns including 2001 and 2008, the technology industry emerged on the other side stronger and more powerful and it had before those recessions. …


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It’s a tough time, markets are changing. Some companies are growing, some are shrinking.

As former scrappy entrepreneurs ourselves, we decided to create an open community job board to connect those hiring and those seeking new roles. Pardon the potential “cold start” here as we are doing this in real-time, but please post and bookmark the page. We hope to help bridge connections ASAP.

If you’re hiring, look here

Affected by the layoffs? Join here

Having been involved in many of these types of adjustments in our own portfolio, we can say that it’s not that companies just “kept the good people.” Entire strategies have changed, entire departments or efforts have been deprioritized. Startups at different stages are pivoting. A founding technical architect at one of our very successful companies has decided to leave so as to give his creation more runway to grow, another company is pivoting product strategy to adjust to an opportunity created by the focus on cost savings and will let go of their entire marketing department. …


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By: Issac J Roth, Partner, Shasta Ventures

I still vividly remember the scene in early November 2008: I was raising money for Makara (which became Red Hat OpenShift.) I arrived 10 minutes early at the office of a well known VC on Sand Hill Road where I was scheduled for a first meeting and… I found all six partners plus various other staff waiting for me in the lobby! I was elated — I only had an appointment with one partner.

Then I realized they were all glued to the TV in the lobby watching CNN for that day’s market news. Not a person even noticed as I walked in. The partner with whom I had an appointment was gracious and met with me, but it was clear from the glazed over look of everyone that I wasn’t likely to get them excited about our vision for containerizing web applications. …

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Shasta Ventures

We put entrepreneurs first -supporting bold innovative thinkers who thrive on building great products and end-user nirvanas.

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