Why I invested: A writing series on early stage angel investing chronicling the rationales behind various early stage tech bets by Pete Kazanjy.

Zum’s a cool story of how a “B2B-lite marketplace” turned into “B2B Heavy” in the realm of student transportation, to substantial upside.

As context, I had been friends with the guys at Chariot, and was always intrigued by the idea of better mobility solutions through smarter routing, purpose made hardware, and such. Unfortunately, Chariot was going up against a myriad of other solutions: Uber / Lyft, mass transit (e.g. San Francisco’s MUNI and BART), professionals driving themselves, bicycling, etc. A lot of competition. (They were eventually acquired by Ford and later shut down. Tough business for sure.). But helping those guys out here and there put the bug in my ear about better “micro-mass mobility” solutions through better tech.

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Why I invested: A writing series on early stage angel investing chronicling the rationales behind various early stage tech bets by Pete Kazanjy.

While I’m not as much of a consumer marketplace investor (B2B SaaS and B2B Marketplaces are more my thing), I am friends with the founders of Instacart, and always kicked myself for missing early rounds of theirs. That, and my last software company was in the same portfolio as Uber at First Round (the outcomes were just a smidge different…lol). Anyway, I’m somewhat familiar with the power of consumer marketplaces that tip.

In 2016, when I saw Rappi’s Series A on Fundersclub, it made me think about the components of what makes a killer on-demand marketplace - and realized as long as the supply side has human components to it, then the higher the Gini coefficient of a market (that is, the more low income folks who are eager to act as on-demand...

Why I invested: A writing series on early stage angel investing chronicling the rationales behind various early stage tech bets by Pete Kazanjy.

After TalentBin was acquired by Monster, one of the things we were tasked with doing was bringing composite profile talent search to other talent categories beyond software engineering.

One of these was healthcare, specifically nursing. We crawled every state’s database of registered nurses and did clever things to append email addresses and other communication vectors. But when we went to sell it to recruiters at health systems and hospitals, they looked at us like we were crazy pants that a recruiter would proactively reach out to a candidate uninvited. Our offering was not viewed, um, favorably. I quickly realized that healthcare recruiting was 10-20 years behind tech recruiting.

And it made sense they were behind the times. Before the...

Why I invested: A writing series on early stage angel investing chronicling the rationales behind various early stage tech bets by Pete Kazanjy.

I owe my investment in Faire to my wife. Before she went back to school to do a graphic design degree, she was a buyer for Williams Sonoma, one of the most impressive merchants in the world. The way they sourced products was medieval. Catalogs and trade shows and faxes and more. She would have to travel to Chicago twice a year to mill around in a massive exhibit hall. Fly to China. Fly to India. And this was the best organization in the world at this. Yikes.

So when I was initially introduced to the Faire team in 2016 (“Indigo Faire” at the time - cutest name ever) by my friend Lauren Farleigh, founder of Dote, I was primed to comprehend what they were working on. (I had worked with Lauren closely on Dote, and she thought I could be helpful...

Why I invested: A writing series on early stage angel investing chronicling the rationales behind various early stage tech bets by Pete Kazanjy.

From my time at TalentBin I was very familiar with the HR / Talent Management Suites that were cobbled together acquisition frankensteins (Successfactors, Taleo, Cornerstone, etc) and could only service large orgs because of their high implementation costs and outside sales motions. Many of them had gone on to be very large outcomes. But it was unlikely that with their level of complexity they would ever be able to service the lower segments of the market.

All that said, talent management - the practice of making the people who make up an organization better at what they do was a powerful promise - especially in organizations where the people were the most important part of the business (knowledge worker organizations).

It was clear there...

Why I invested: A writing series on early stage angel investing chronicling the rationales behind various early stage tech bets by Pete Kazanjy.

I love Airtable. It’s such a killer product, and since I invested in 2017 I’ve only come to love it more and more. I’m an unapologetic homer in the worst way.

I knew Howie from Crowdflower, and then after his eTacts business was acquired by Salesforce he met with me to talk strategy when Salesforce was briefly looking at potentially acquiring TalentBin.

Later on Ben Cmejla from First Round Capital introduced me to the Airtable product, and we started running parts of Modern Sales Pros out of it, and that was the point that it really started clicking for me.

It was very clear quickly that Howie had taken the promise of point and click development from Salesforce (which as someone who is a pretty good Salesforce admin, Salesforce is not...

Over the last 8 years since my first software company, TalentBin, was acquired by Monster Worldwide, I’ve become a fairly frequent angel investor.

I’d love to say it was because I thought it was a surefire path to financial improvement - but the actual truth is that I find it quite intellectually compelling - combining problem solving, leveraging existing expertise, learning new things, and other things that I consider best in life. So I’ve probably ended up doing more than was probably wise.

Over the last nearly decade I’ve invested in north of 100 individual companies during my nights and weekends, and have certainly learned a lot along the way. And not done terribly at it either, with a handful of 20x realized outcomes, and even some 50x, 100x and even 500x markups (fingers crossed!). Not to mention, of course, a good number of investments that have gone to zero.

But despite...

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Pete Kazanjy (LinkedIn, Twitter) is a serial founder, and seasoned early stage Saas executive, advisor, and investor. Pete founded TalentBin, a category-defining talent search engine and recruiting CRM, which exited to Monster Worldwide in early 2014. Pete currently is the founder of Atrium, makers of data-driven sales management software, author of Founding Sales, the definitive Startup Sales Handbook, and founder of Modern Sales, the nation’s largest sales operations, leadership, and enablement community.

At TalentBin, Pete went from product and product marketing founder generalist, to first sales rep, first sales manager, first VP of Sales, all the way to leading new product sales for 600+ sales reps at Monster worldwide. After Monster, he wrote a book on startup sales for founders and other first-time sellers, Founding Sales, documenting...

As anyone who follows me on Twitter knows, I am quite possibly First Round Review’s 1 fanboi.

The combination of relevant, actionable, and true information, delivered in such a well executed package is unparalleled. And when you compare it to the absolute sea of bullshit self-promotional content marketing (both VC and vendor) that founders have to otherwise contend with when trying to get insights to tackle day to day problems, First Round Review starts looking less like a VC publication and more a community treasure.

That, and Camille Ricketts and Shaun Young are just absolute delights.

My Favorite Review Articles

So, the other day I was tweeting about how I seem to end up following up every startup coaching meeting I have with a handful of links to First Round Review articles that, if applied properly, will help solve the problem(s) the person I’m coaching has.

My friend Tyler...