Rachel Spekman is currently the Director of Programming at MassChallenge, which describes itself to be the most startup-friendly accelerator on the planet. MassChallenge awards over two million dollars in equity-free prizes every year to help high-impact startups succeed.

In this episode, Rachel talks about:

What sets MassChallenge apart from other accelerators

What the curriculum looks like and which mentors are available

Traits she has noticed in the most successful founders

Advice for founders applying in MassChallenge

Links from today’s episode:

Rachel Spekman on LinkedIn

Rachel Spekman on Twitter

MassChallenge

PULSE@MassChallenge

Resilient Coders

A Truck Full of Money

Zero to One

Steve Jobs Biography

Americanah

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

Semyon Dukach is currently the Program Director at Techstars Boston and is an angel investor with roughly over 100 investments. He is also the chairman of SharpSpring, which he took over in 2002 and then took public in 2011. He lead one of the MIT blackjack teams in the early nineties, has started a few companies, and in 2012 Semyon created “The Troublemaker Award”.

In this episode, Semyon talks about:

His time leading one of the MIT blackjack teams in the nineties

Why he loves investing in startups and what he looks for

Why he took a company public in 2011, despite not needing to raise money

Advice he would give to someone applying to Techstars

Why he created “The Troublemaker Award”

Links from today’s episode:

Semyon Dukach

SharpSpring

AccuRev

Techstars Boston

Troublemaker Award

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

Rob MacLeod is founder of Neoscape, a one-stop shop for clients including real estate developers, architects, designers, and corporations for everything from 3-D renderings, imaging, filmmaking, animation, interactive development, branding, and strategy. Rob was a full-time carpenter and went to school for architecture before founding Neoscape twenty-one years ago.

In this episode, Rob talks about:

Virtual reality, including where Rob sees the field going and how Neoscape’s clients use the technology

What Rob’s hiring process looks like and what characteristics he looks for

Failures, specifically a quote by Rob where he says, “Failure is necessary for a company and for personal or employee growth.” (Article linked below)

How Rob stays excited by the industry for being in it for over twenty years and how he stays hungry to pursue new technology and techniques

Links from today’s episode:

Neoscape

“If I Knew Then…” –Rob MacLeod

Magic Leap

Mavenlink

Soldier Design

Gary Vaynerchuk Blog

Wired

Good to Great

The One Minute Manager

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

Enrico Palmerino founded botkeeper to focus on the software solution for bookkeeping by using artificial intelligence. Enrico started his first company ThinkLite while attending college at Babson. ThinkLite is a lighting designer, manufacturer, and installer that allows customers to pay for lighting solutions as a percentage of their savings with no upfront costs. After ThinkLite, Enrico was co-owner and managing director at SmartBooks and eventually founded botkeeper. In 2011, Bloomberg Businessweek named him second in the Top 25 Entrepreneurs Under 25 and he has also had both of his previous companies named to The Inc. 5000 and The Inc. 500, respectively.

In this episode, Enrico talks about:

Artificial intelligence: what scares him the most for its future, what excites him the most for its future, and resources for people who are new to artificial intelligence and machine learning.

Lessons he learned at his previous companies that he’s applied at botkeeper

What drives him and what he believes makes an entrepreneur successful

Why you shouldn’t be nervous to have a bot handle your company’s books

Links from today’s episode:

Enrico Palmerino

Email Enrico

ThinkLite

SmartBooks

botkeeper

MarketMuse

Talla

Bill.com

Trello

Expensify

QuickBooks

The Checklist Manifesto

The Fish That Ate the Whale

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Music by: Broke For Free

Maya Rafie is founder of Bistara, the first freelance marketplace to hire college students for creative gigs. Maya, a freelance photographer, founded Bistara while attending Emerson College. Bistara encourages students to “be your own boss” in order to build up a portfolio of work prior to graduation. Today, there are over 700 freelancers and over 300 clients on the platform.

In the episode, Maya talks about:

How they originally started building out the marketplace for Bistara

The experience of starting a company in college

Why students have a hard time valuing their talents and how they can overcome it

Tips for clients and freelancers to be more successful on the platform

Links from today’s episode:

Bistara

Maya’s Photography

Trill

Elliott Erwitt

Lightroom

Google Calendar

Asana

WhatsApp

Les eaux troubles du mojito : Et autres belles raisons d'habiter sur terre (Book)

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Music by: Broke For Free

Doug Morgan is the Director of Engineering at Lola Travel. Doug joined the company when Lola acquired HopOn, the company he co-founded. Lola connects travelers with in-house personal travel consultants who help customers plan, book, and manage their travel in an effort to make trips more personal and rewarding.

In this episode, Doug talks about:

The process of being acquired

The transition from founder to employee

The key to building a successful engineering team

Lessons from SurveyMonkey and HopOn that he applies at Lola

Links from today’s episode:

Doug Morgan

SurveyMonkey

HopOn

Lola Travel

Lola Travel (App)

Trillium Brewing

Harpoon Brewery

Jack’s Abby

Drafted

Drizly

Fitbit

Slack

First Round Review

Both Sides of the Table

The Atlantis Gene (Book 1)

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

Win Smith’s father was a founding member of Merrill Lynch and he worked there for twenty-eight years as the executive vice president. However, when new management was brought in and disagreed with the values that the firm had been founded on, he left. Win moved from New York City to Warren, Vermont to run Sugarbush ski resort full-time, which he had purchased a few years prior. At the time, Sugarbush was nearing bankruptcy, but thanks to investments made by Win and others they were able to turn Sugarbush around to the thriving ski resort that it is today.

In this episode, Win talks about:

The importance of the governments EB-5 program in reviving Sugarbush and bringing it to profitability

How they are shifting their approach as their clientele shifts from baby boomers to millennials

What it was like to completely shift careers at age fifty-five

Links from today’s episode:

Sugarbush

Win Smith

Catching Lightning in a Bottle

Alpine Zone

Framed: Why Michael Skakel Spent Over a Decade in Prison For a Murder He Didn’t Commit

Maverick Mountain

Telluride Ski Resort

Steamboat Mountain

Aspen Highlands

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

 Rory Crawford is co-founder and CEO of BevSpot. BevSpot is a hospitality management software that allows restaurants and bars to monitor and order inventory three times faster and provides visualizations to help identify trends in usage, inventory, profitability, sales, and variance.

In this episode, Rory talks about:

Why building out a prototype allowed him to stand out and attract co-founders

Biggest trends happening in the bar and restaurant industry

Why they wanted to make BevSpot a SaaS (Software as a service) product

What has been keeping the hospitality industry from adopting data-driven, decision-making tools

Rory Crawford

BevSpot

Catalant

SaaStr

Autobiography of Martin Luther King, Jr.

Biography of Winston Churchill

Biography of Albert Einstein

Biography of Benjamin Franklin

No.9 Park

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

Cort Davies is founder of StartupCMO, an aid to small companies with limited budgets for marketing. Cort first got into online marketing after realizing that the Internet was the next big platform after real estate. After helping friends generate leads for their companies, Cort founded StartupCMO to help more companies with marketing budgets too low to hire someone full-time, but adequate enough to still achieve great results. Along with his primary passions, Cort is also a mentor at MassChallenge and has helped over fifty startups.

In this episode, Cort talks about:

Where marketers should focus their attention

What people who are new to marketing waste their time doing

How founders can find product/market fit faster

Trends he sees happening now in digital marketing and how to take advantage of them

How to build trust with a potential customer

Links from today’s episode:

Cort Davies

MassChallenge

TakeLessons

Oath Pizza

Habit List

gTasks

RPM

Calm

Tim Ferriss

Tony Robbins

HelpSpot

Jay Abraham

The 4-Hour Workweek

Awaken the Giant Within

You Are the Placebo: Making Your Mind Matter

The Power of Habit

Brian Tracy

If you liked this episode:

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free

Karin Brandt is founder and CEO of CoUrbanize. CoUrbanize allows residents to participate in the development process of their neighborhood. Ideas can be exchanged and considered without having to physically go to meetings and sort through piles of paper.

In this episode, Karin talks about:

What the Techstars experience was like for her

The benefits of CoUrbanize for real estate developers and municipalities

How planners and developers can go about getting engagement from the community

How they are using sentiment analysis to better understand the communities’ feelings

Links from today’s episode:

CoUrbanize

TechStars

ArtLifting

Evernote

Junot Diaz

AVC

Joanne Wilson

If you liked this episode:

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Get in touch with feedback, ideas, or to say hi: nic {AT} startupbostonpodcast [DOT] com

Music by: Broke For Free