Shane Mac, a Silicon Valley transplant from his hometown of Pekin, Illinois, is a master of building authentic relationships based on trust and personal connection. In fact, he’s so good at winning people over with his honest Midwestern brand image, that he’s learned how to raise capital without ever asking for money.

I met Mac a few years ago at the Big Omaha conference in Omaha, Nebraska, and he’s consistently blown me away with his ability to grow funded companies ever since. He’s worked on the Gist and Zaarly teams, and he now runs Assist, a free-to-use travel and shopping chatbot for SMS and Facebook Messenger. This interview was recorded early last year, shortly after Mac closed a $5.5 million Series A round for Assist, which he achieved based on the strength of his professional relationships alone.

Mac believes relationships are the backbone of any business venture, and he’s a devoted practitioner of what he preaches. In our interview, he shares counterintuitive but proven strategies for creating authentic connections and gaining interest in your business. He believes in closing fundraising rounds by consciously refraining from making a direct ask. He also regales me with a too-crazy-to-be-made-up story of how he closed Assist’s $500,000 seed round in five days—over a holiday break.

If you like the wit and wisdom Mac shares in this interview, be sure to check out his podcast, ask., as well as his very unique and enlightening business book, Stop with the BS. Mac is very active on social media, so feel free to reach out to him on Twitter, Instagram and elsewhere @ShaneMac.

In this episode with Shane Mac, you’ll learn:

  • Why the best way to raise money is to avoid asking for it (7:05)
  • Step-by-step strategy for attracting investors, including one crazy success story (11:08)
  • How to build authentic business relationships based on trust (21:55)
  • Asking someone to tell their story is the best way to get them interested in you (32:24)
  • Why humility and gratitude are the keys to an outstanding pitch (40:56)
  • Actionable tips for making potential collaborators like you (50:06)

Please enjoy this conversation with Shane Mac!


This episode of Powderkeg is brought to you by DeveloperTown. If you’re a business leader trying to turn a great idea into a product with traction, this is for you.

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Shane Mac Quotes from This Episode of Powderkeg:

Links and Resources Mentioned in this Episode:

Companies and Organizations:




The Kauffman Foundation



Geek Squad

Lonely Planet

Venture Capital Firms:


Binary Capital


Big Omaha


Stop with the BS

Software and Applications:







Shane Mac (@ShaneMac)

T.A. McCann (@tamccann)

Bo Fishback (@bowman)

Dennis Phelps (AngelList)

Ken Kamada (AngelList)

Galen Buckwalter (@jgbuckwalter)

Andrew Warner (@AndrewWarner)

Bryan Johnson (@bryan_johnson)

Jason Fried (@jasonfried)

Gary Vaynerchuk (@garyvee)

Robert Stephens (@rstephens)

Jonathan Teo (@jonteo)

Justin Caldbeck (@caldbeckj)

Daniel Houghton (@danielhoughton)

Sam Shank (@samshank)

Keyvon Beykpour (@kayvz)

Chase Jarvis (@chasejarvis)

Did you enjoy this conversation? Thank Shane on Twitter!

If you enjoyed this session and have 3 seconds to spare, let Shane Mac know via Twitter by clicking on the link below:

Click here to say hi and thank Shane on twitter!


What stood out most to you about what Shane shares in this podcast?

For me, it’s how to build authentic business relationships based on trust.

You? Leave a comment below.


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