It’s not where the Sox play ball.  It’s home to the world’s largest accelerator, MassChallenge, where 128 start-up businesses from around the world are polishing their plans and getting mentored in hopes of winning money or landing that critical investor audience.

I just finished leading my third program on how to pitch.  The finalists are far enough along that they no longer get allowances for unknowns and the chance to engage a listener with information they only hope to hone.  They’ve done enough homework to know their team needs, round out their data, show they’ve tapped the right market, trot out validating customers, or boast a board of advisers.  Yet even the most brilliant entrepreneur can get caught in the headlights.

Here are the six tips that the companies I’m coaching will hear from me in the coming weeks:

1.  Educate.  You have two parallel shots to draw in your audience.  Converse like an excited or impassioned human.  And make sure your slide titles advance your plot.  Investors who learn something interesting — even complicated — will remember your company.  But easy on the details or the science — you still have to pretend that you’re explaining the business to your great aunt.

2.  Differentiate.  What makes your organization especially well-positioned to maximize the available opportunity?  Have you protected intellectual property? Do you have a unique R&D strategy or operational efficiency?  Can your team rein in chaos, productize and sell?

3.  Market. A product or service that “sells itself” (because it’s an app that’s sure to go viral and there are a billion smartphones) almost never happens. Offerings should dovetail with industry or market trends.  Have a nuanced rendition of who will pay what for it and the existing sales or other channels that will likely get it to them.

4.  De-Risk. In start-up parlance, each step of identifying and overcoming potential vulnerabilities, surpassing intermediate milestones and boosting credibility is referred to as “de-risking.”  A great idea in and of itself rarely wins the day.  You must show through team building, partner relationships, patent filings, customer testimonials or otherwise that you’re on a course that is both systematic and productive.  If you’re at square one on drug discovery, get a credible board of advisers.

5.  Project. The right balance between aggressive and conservative financials is tricky.  The key is expertly identifying assumptions and risks underlying your traction and scalability.  This is a good place to identify shortcomings or challenges too.  Nothing worse than getting beat up by an angel for being perceived as un-coachable.

6.  Budget. How much are you looking to raise?  In what form?  Be prepared to describe the development, manufacturing, hiring, marketing, distribution, or sales you can reasonably accomplish with that amount (or a fraction of it!).

Ready to knock it out of the park?  See you at the finals!

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Photo of Jonathan Shamay-Draluck Jonathan Shamay-Draluck

Jonathan Shamay-Draluck is a seasoned transactional attorney who has led complex, high-value arrangements on behalf of, or opposite, dozens of Fortune 100 companies.

With a particular focus on the rapidly growing digital infrastructure industry, Jonathan has represented investors, hyperscalers, developers and others in

Jonathan Shamay-Draluck is a seasoned transactional attorney who has led complex, high-value arrangements on behalf of, or opposite, dozens of Fortune 100 companies.

With a particular focus on the rapidly growing digital infrastructure industry, Jonathan has represented investors, hyperscalers, developers and others in data center construction, leasing, and the full range of ancillary commercial arrangements. He has also negotiated deployment of subsea and terrestrial fiber and supported operation of data network elements around the globe.

But his broad technology practice has brought him to serve in a variety of roles including as outside and in-house counsel to technology companies and IT consulting firms, leading efforts to align proprietary offerings, professional services and third-party systems, helping them to enable enterprises to leverage AI and other high-throughput platforms.

Extending his transactional capabilities beyond the technology sector Jonathan has represented pharmaceutical and medical device companies as they negotiated M&A, sponsored research, clinical trials, technology transfer, patent licensing, and manufacture agreements. He also counsels startups on formation, securities issuance, intellectual property protection, compliance, go-to-market contracting, and sale of control.