Amy Errett is CEO and Founder of Madison Reed, a startup revolutionizing every aspect of the home hair care experience. Amy founded Madison Reed with years of business and operating expertise as a leading entrepreneur, senior executive, venture capitalist and social-mission visionary, under her belt. Previously she was a General Partner and ran the Bay Area office of Maveron - so you know she's seen a good investor pitch or two. Prior to Maveron, Amy was the CEO of Olivia, repositioning the travel business as a complete lifestyle company - so she's got solid operating experience (proof in point: Olivia, Amy was named the Ernst & Young Entrepreneur of the Year for Northern California). As for previous 'founder' experience, Amy founded and successfully "exited" The Spectrem Group, a worldwide strategic consulting, information, and M&A advisory firm. So, what possibly could Amy do wrong....

Amy admits, despite all she knows as an operator and investor, she's guilty of hiring too quickly then, regretting it and not firing quick enough when she knew it was not working out. Her recommendation at the end of the day (and advice from arm-chair CEOs) is always to trust your own judgment.

When it comes to mistakes made in the pitching process, Amy strongly suggests paying close attention to every mistake you've made and really listen to others about their mistakes - sometimes investors aren't to blame when the pitch goes sour. On which investors to pitch, look for patterns (from the number of pages in a pitch deck to how a pitch meeting is conducted) - yes, pattern recognition may be to your pitching advantage.

Amy's advice is that you get comfortable with "always" pitching. Her top recommendations:

1. Remember every interaction in the startup community is an opportunity to explore how that connection can help your business (even if you're not raising money or hiring at that exact moment).

2. The best time to pitch is usually right in front of you (at that conference, meetup or social event), you just need to pay attention!

3. Your focus isn't to pitch at every encounter. Instead what you should focus on is making connections by listening, telling your story plus asking others for guidance and thinking of ways you can help them with their venture. As Amy knows everyone needs help, including investors.

Matt Fiedler is CEO and co-founder of Vinyl Me, Please, a record subscription service, which has grown since from 12 paying members when founded in 2013, to currently having over 20,000 paying members. Matt graduated from Belmont University in 2011 with a dual degree in Music Business and Entrepreneurship. After working a number of jobs in the tech and music industry from 2011-2014, Matt quit his day-job to run Vinyl Me, Please full time in July of 2014.

While Matt has bootstrapped Vinyl Me, Please to date, he has had pursued meetings with potential investors as well as advisors in order to prepare for "the talk" with investors. Through those conversations, Matt's refined his pitch - along with gaining clarity of his mission, vision and strategy for Vinyl Me, Please. For other entrepreneurs, Matt shares what investors are seeking to understand from your pitch:

· Mission: Why your startup exists

· Vision: What you want the startup to become

· Strategy: How you as founder and CEO will get there

Yes, "pitching" investors for advice (before you need to raise money) has its benefits.

And these pre-pitch conversations have had additional benefits for Vinyl Me, Please. For example, Matt meets regularly with his leadership team to have structured conversations around the vision for the company. As a result they are more aligned in their decision-making ("all working off the same sheet of music" says Matt). These meetings have facilitated some difficult conversations - all been for the betterment of the team and the company.

Matt's suggestions on "always be pitching":

· Don't start by "pitching". Some of the best and most fruitful conversations you'll have about your startup will come from casual encounters. No deck, no financials, just talking about what you're doing - but don't approach the prospect of these conversation casually, always be prepared to talk intelligently about your startup.

· The best luck comes from leaning on your personal network - so make building relationships in the startup community a priority from the first day of your venture. Matt also notes that he's never ever made a connection with the intent of asking for money, only asking for advice. And that advice conversation has usually led Matt down the route of talking about money. Again proof of the wisdom that "If you ask for money, you'll get advice; if you ask for advice, you'll get money"