While just one in 10 VC investments achieves a successful exit or next stage funding, a small team of upstarts has quietly come up with a way to significantly increase the odds of identifying whether a startup has a decent shot at succeeding.

After two years of internal work, the Microsoft Startup Predictor has proven to have a 75% success rate in predicting a future funding event.

The Startup Predictor is an AI-powered prediction engine conceived and developed by Series A – The Podcast host Jim Brisimitzis, Sonal Mane and Pushpraj Shukla.

In this edition of Series A, the trio detail development of the tool that can save VC’s millions of dollars by providing them an exclusive tool to dramatically increase the success of their investments.

Developed by a startup team inside Microsoft, the Startup Predictor combines the power and expertise of the Microsoft Startups group in the United States and Canada and the Microsoft Market Intelligence & AI team.


Can a company change the face of advertising while doing good at the same time?  The founders of Chicago-based Do Good Media are doing just that.

In this edition of Series A – The Podcast, we visit with co-founders Jerome Shimizu and Michael Sheng during a visit to startup epicenter 1871.

“We provide publishers with billions of high-quality, incremental advertising opportunities,” the company says.   But what exactly does that mean?  The answer depends on the customer, Sheng says.  At its core, Do Good is doing some amazing things across various media sectors to deliver new solutions and value in the cut-throat and ever-changing world of advertising.

As experienced founders and executives, Shimizu and Sheng offer valuable insights for any entrepreneur, from innovation to building an organization.  Join technical evangelist Martin Schray and producer/correspondent Josh Kerns for a wide ranging and thought provoking conversation in the latest edition of Series A – The Podcast.


What do you get when you combine a seasoned serial entrepreneur and technologist with a PhD and tenure track cancer researcher at the University of Chicago?  One of the most promising startups disrupting the health care industry.

In the latest of edition of Series A – The Podcast, we return to Chicago for a visit with Jason Smith, the co-founder and CEO of rMark Bio.

Smith’s diverse background provides for an insightful and wide-ranging conversation spanning over 17 years of experience doing everything from raising millions in capital, leading a number of ventures and serving as principal technologist in distributed systems architecture, big data analytics, and high-performance computing from work with ATI Research, AT&T, General Dynamics, IBM and GraySky Simulations.

rMark Bio’s industry leading AI solution understands the real-time business strategies of R&D, Medical Affairs, Marketing, and Commercial to provide field representatives with clear and concise ‘next best decisions’ that remove inefficiencies and increase ROI for thought leader engagements, the company says

“Leveraging artificial intelligence, we can go beyond the who.  We can tell you why you should be engaging with them from a business perspective, what you should be engaging about when we tap into your content management systems, how this will help your business based on knowing your strategic KPI’s and strategic goals for a given quarter or year or even a year, and really what are the next best actions if you’re a field rep to meet those goals,” Smith tells technical evangelist Martin Schray and producer/correspondent Josh Kerns.


When Expedia founder Rich Barton was secretly building Zillow, it was Seattle tech news site Geekwire that first uncovered and broke the story.  Same with the first tests of Amazon foray into the grocery business and numerous other big tech stories.  That dogged reporting is why the Seattle-based enterprise has become the preeminent voice of technology in the Northwest – attracting readers from around the world.

“We founded the company – the startup – on the premise that Seattle and the Pacific NW deserved an international tech site,” says co-founder Todd Bishop.

Bishop and staff reporter Taylor Soper share their experiences and insights with host Jim Brisimitzis on the latest edition of Series A – The Podcast.

Their stories offer valuable teachings for any entrepreneur as a startup that emerged successfully from the massive disruption in the media world to become the most influential source of information and community for Northwest tech companies from Microsoft and Amazon to the smallest of startups.

“From the beginning we knew that digital advertising was not going to be enough to fuel the business. I think that was one of the biggest mistakes media companies were making at that time [Geekwire founding} , assuming they could just write enough stories and get enough clicks that they could use advertising networks to pull in enough revenue to sustain the business,” Bishop says.

The company has supplemented its revenue stream with other offerings including up to a dozen events a year from the highly attended Geekwire Summit to small, private dinners bringing top tech execs together.

Bishop and Soper also offer their valuable takes on hot topics such as Seattle’s controversial head tax targeting tech companies like Amazon to tackle growing income inequality and homelessness blamed on massive growth.

“My big take is that technology companies needed to have been engaged on the larger issue this is trying to address much sooner in the process,” Bishop says.

“If you’re having a conversation about your next 20 or 30 or 50 developers and there’s all of a sudden this new tax, you’re maybe rethinking that decision. This is what the CEO’s are saying,” Soper adds.
need for more startup funding if ecosystem is to grow

Bishop and Soper offer expert perspective on the differences between Seattle and Silicon Valley, the challenges facing founders now and in the future.  And they provide revealing insights into what it takes to get that all important media coverage companies crave – all too often common sense but overlooked.

“First of all, make sure your product works, make sure your website works, make sure the buttons on your app work,” Soper says.




When it comes to representation and funding for minorities in the startup world, the numbers are sobering. Less than 3% of venture capital goes to female led startups, while just .02% (you read that right) goes to startups led by women of color. And there are so few Hispanics given the opportunity to lead a company or acquire capital, there aren’t even statistics for them.

That’s why the work of organizations like Project UK (United Knowledge) are so critical. In the latest edition of Series A – The Podcast, we travel to Kansas City to visit with Quest Moffat, founder of what he dubs a startup studio.

It’s far more than just an accelerator. Moffat outlines how Project UK is working to provide resources to founders struggling to validate their business ideas, by providing capital and counsel to aspiring entrepreneurs, especially those of color.

In a frank discussion with Microsoft technical evangelist Jordan Svencara and producer/correspondent Josh Kerns, Moffat details the radical approach and breakthrough successes Project UK has fostered by bringing capital and knowledge to those who otherwise be shut out. And he outlines why huge advances in breaking down barriers are happening in the Silicon Heartland, not the Valley.

“Looking at the deals, our deals in Kansas City were holding the same percentage of investments into women and people of color as Silicon Valley, Boston and New York. And so we took it upon ourselves to say ‘what can we do to solve it’,” Moffat says.

Listen now for thought provoking insightsinto into the challenges facing minority founders, and the innovative solutions fostered by pioneers like Quest Moffat at Project UK in Kansas City in the latest edition of Series A – The Podcast


How do you make watching sports and other events truly social, and build a successful business for major media companies at the same time?  For Game On co-founder and CEO Alex Beckman, it’s all about the bots.

The problem to solve for the San Francisco-based startup is  figuring out how to get people to watch content they want to watch on the devices they want to watch it on without making the assumption that because it was done a certain way on TV that’s how it should be done online, Beckman says.

“Maybe four or five years ago we began to really see people distinguish between digital and mobile and understand that digital is not mobile. And now we’re seeing that mobile is not a thorough enough term,” Beckman tells host Jim Brisimitzis in the latest edition of Series A – The Podcast.

Beckman shares stories of growing up in the epicenter of the technology world in Silicon Valley, with classmates named Ellison and the like showing a second generation of genius from a young age.  While Beckman could hang with them, coding wasn’t his calling.

“I was a bad developer. I didn’t love sitting down and writing code,” he laughs.

Lucky for him, his love of film and technology led to him instead to build a successful business he sold to Yahoo just nine months later.  But he and his co-founders recognized they had far more work to do.

Beckman details the lessons learned building a product and company, successfully exiting, then going it alone a second time.  He admits he made plenty of mistakes, and is trying to enjoy this go-round far more.

In the wide ranging and insightful conversation, he dispenses plenty of hard earned advice for fellow founders and would-be entrepreneurs.  Surprisingly, that going it alone isn’t the answer.

I think everybody should have two co-founders because the odds of two people having a bad day on the same day are high, but that third just gives you the chance one of you is not having a bad day, and silly as that sounds that probably saved.

Check out Beckman’s conversation with Brisimitzis on the latest edition of Series A – The Podcast


For every deal, there’s a document.  Actually, potentially hundreds of thousands or even millions of them.  But thriving Chicago startup Heretik is leveraging AI to help the legal world search, sort through and analyze contracts, dramatically cutting the time and money spent in contract review.

The work has always been done manually, with lawyers and paralegals opening documents one at a time, reading each clause, section or paragraph, then copying and pasting into Excel for review.

“It’s a very tedious process. It takes weeks, some times months to go through, and we’re bringing in some artificial intelligence to streamline that to take those months down to days, sometimes hours,” says Andy Abbott, co-founder and CTO of Heretik.

Abbott is the featured guest on the latest edition of Series A-The Podcast, recorded at 1871 in Chicago.

“For global enterprises, any deal can mean hundreds of thousands if not millions of documents for complete viewpoint of risk and obligations,” Abbott tells Microsoft technical evangelist Martin Schray and producer/correspondent Josh Kerns.

It’s his second venture as a founder.  His first company Booked Out was acquired by Shiftgig, leaving Abbott wondering what to do next.

“I realized I didn’t want to work at a larger company. I still wanted to do that entrepreneurial thing,” he says.

Abbott’s experiences have served him well with his new venture.

“Obviously the second time you have a lot of lessons that you’ve learned, mistakes that you’ve made previously and it is easier,” he says.

Abbott offers a myriad of insights for his fellow founders, from product development to sales.  His revelation the company created no code for months while connecting with potential customers and truly understanding their needs before building a solution is among the eye-opening tidbits.

“What happens a lot is you focus on building that product first and then when you go out to share it, to give it to your customers, you hit these roadblocks.”

Abbott also details lessons learned bringing disruption to old-school industries like the legal field used to doing things manually.

“If you’re going to introduce change or bring in technology to a space that isn’t used to it, they’re going to push back. And so how can we reduce that push back?”

Listen to the latest edition of Series A-The Podcast to learn how Heretik is overcoming that, and making a major mark on the law.


If knowledge is power, then Chicago-based startup Packback is rocket fuel for college students blasting off into the future (excuse the cheesy analogy, but it’s apropos in this case.)

In the latest edition of Series A – The Podcast, hosted by Jim Brisimitzis from the Microsoft for Startups team, we profile the dynamic startup changing the way college students and their professors share information and knowledge to help empower fearless, relentless curiosity.

“Instead of just focusing on memorizing facts, Packback Questions is the place where you can ask the big, sometimes unanswerable, questions that you’re truly curious about,” says Jessica Tenuta, co-founder and chief product officer, in a wide-ranging conversation with technical evangelist Martin Schray and producer/correspondent Josh Kerns.

Tenuta offers keen insights into the company developed by a group of college students, now reaching tens of thousands of students nationwide.  Packback builds artificial intelligence to quantify and improve difficult-to-measure student success metrics at scale — such as student critical thinking, soft skills and curiosity — by analyzing a student’s written questions and essay answers. Their product Packback Questions is a “smart” online discussion platform powered by their AI, where students engage in rigorous academic discourse as a core part of their instructor’s curriculum and coursework.

Tenuta details how the company’s commitment to its core values drive all of their decisions, from product development to hiring – often passing on top tech talent if they don’t seem like a good fit for the culture.  She also provides key lessons for other founders on recognizing when to pivot, how to work best with multiple co-founders (in their case, four), and she reveals the company’s true secret to success: Pepper the Packback pup.

Despite barely being old enough to rent a car, Tenuta and her team are bringing a major change to ed tech, and their experience and enthusiasm or extremely valuable to anyone looking to learn from truly pioneering founders.


Attending a conference, meetup or gathering and coming away without making valuable contacts is an all too common and frustrating occurrence for busy business people.  But Chicago-based Proxfinity is shining a literal light on the problem – with a unique wearable and software solution.

In this edition of Series A – The Podcast, meet Lisa Carrel, co-founder and CSO of the company bringing real change to the conference world.

Carrel shares the journey of Proxfinity with Microsoft for Startups technical evangelist Martin Schray and producer/correspondent Josh Kerns, detailing a unique path that included patenting a product before there was really even a market.

In a nutshell, Proxfinity’s solution features a smart badge that lights up to identify common interests and allow people seeking to make connections a quick and easy way to identify someone they should speak with.  It sounds simple, but it’s an elegant, complex and effective way to maximize the time and efficacy of a networking event.

Carrel offers valuable insights and advice for other female founders on everything from raising capital to building a team, and chronicles how Proxfinity pivoted several times before settling into its successful strategy and solution.

Even though Proxfinity emerged from a cohort of female-led companies nurtured by 1871 in Chicago, the company’s story, struggles and successes are important teachings from any entrepreneur.



From a smart city to smart apartments, Kansas City entrepreneur Blake Miller has been at the forefront of innovation on the Silicon Prairie.

In the latest edition of Series A – The Podcast, we travel to Kansas City for an in-depth look at why America’s heartland is home to some of the nation’s top tech talent along with arguably its best barbecue.

Producer/correspondent Josh Kerns visits with Miller and Microsoft for Startups technical evangelist and engineer Jordan Svancara to go inside his latest venture Homebase, a smart apartment platform and ecosystem poised to dramatically change the rental housing game for tenants and property managers alike.

“After researching the market, the results were conclusive–current property management platforms aren’t built to handle the needs of today’s connected life,” Miller says.

For residents, Homebase brings together the best of IoT, combining smart appliances, security and the like with rent and utilities payment, maintenance management and more.

Homebase enables far better management for apartment owners as well, from finance to maintenance, enabling dramatic improvements in efficiencies, service and ultimately revenues.

Miller and Svencara also offer an insiders view into what makes Kansas City so special as a pioneer in innovation, from municipal WiFi to fiber to a number of other public/private partnerships that have spurred continued growth and success for the city, entrenched enterprises like Sprint, Garmin and Cerner, and countless startups like Homebase.  And did we mention the barbecue?!


Plenty of people are called industry leaders, tech titans, ground breakers and pioneers.  But few have earned the moniker like Chicago tech visionary Howard Tullman.  The serial entrepreneur has helmed a variety of successful companies, written numerous influential books, and helped spawn hundreds of other companies through his groundbreaking startup collective 1871, the epicenter of the Chicago tech scene.

In a very special edition of Series A – The Podcast, Tullman shared his rare insights and wisdom in an exclusive, in-depth conversation with technical evangelist Martin Schray from the Microsoft startups team in Chicago and Series A producer/correspondent Josh Kerns as he prepares to retire from his role as CEO.

Tullman offered unique perspectives on what makes Chicago such a vibrant economic center, despite often being overshadowed by other cities like NY and San Francisco. (1:00)

“It’s very rare to find an economy where no single part, sector or industry is more than 12 or 13 percent,” he says.

The result is a thriving economy with opportunities in all industries, from logistics to automotive, education to CPG.  And its area universities turn out more computer science and engineering graduates than perhaps Boston, Tullman says.

He offers some provocative but realistic takes on the failings of big enterprises to nurture innovation, creating widespread opportunities for startups – especially in Chicago. (3:10)

“If you look back at the last decade or two, I would say that all of these big corporations starved R&D and now they’re desperate to make it up and they think M&A is going to make it up and that’s not going to happen by itself. It’s going to happen when you have match makers like 1871, when you have people that have developed whole pipelines of opportunities.”

Tullman shares his unique experience in the evolution of Chicago as a tech center, growing from just two percent of the economy when he founded 1871 six years ago (6:00) (named after the year of the great Chicago fire that leveled much of the city, but sparked its renaissance) to 14 percent today.

“In the last five years we’ve added 165,000 jobs that we would call tech-oriented jobs,” he says of Chicago’s growth.

(10:41) Tullman speaks passionately of 1871’s successful efforts to nurture women in tech and Chicago’s place as the leading city for female entrepreneurs, as well as the critical need and value of diversity.

(17:45) Among the other highlights are his perspectives on the challenges and opportunities of new trends, (21:00) his criteria for selecting companies for 1871 or his funds, Why he penned a recent article in Inc. and believes in slowing down some companies and founders moving at the usual breakneck speed of the startup world (30:00), and the use and value of metrics to evaluated performance. (41:00)

It’s a rare and extremely valuable  opportunity to hear from such a titan of tech and business for anyone interested in entrepreneurship, leadership and the Chicago tech ecosystem on the latest edition of Series A – The Podcast.