Sage Summit Day 3: Looking back from perfect

Published · 6 min read

It’s 5:15 in the morning and I’m seriously questioning my judgement. At midnight last night I agreed to go for a run with the Sage team at 5:45. Sleep has been in short supply this week with the jetlag and everything that’s been going on at Sage Summit.

Nevertheless I throw on my gear and head down to Millennium Park. The sun is rising and we all have a great time running together along the shores of Lake Michigan. The Chicago skyline is a beautiful mix of old and new tall buildings glowing in the early morning sun. See a short video of our run here.

Sage Summit 2016

I shower and head into McCormick Place for an early tech rehearsal for my talk. I’m hungry but don’t have the cash for breakfast as I need my remaining $8 to get to the airport on the last day. I suck it up and head into the main hall for the opening keynote. Gwyneth Paltrow will be speaking about her online retail company Goop and Zooey Deschanel is going to share lessons learned from her business Hello Giggles. The talk is to be led by President of Sage in the US, Marc Scheipe.

Each keynote at the Summit has opened with a different Sage executive talking about their personal experiences with small businesses. Mark is a fighter pilot and it’s interesting to hear from him that veterans are 46% more likely to be self-employed and 1 in 10 start-up small businesses.

Marc is then joined by @MikeGoody85 @BrianStann @VickyGoslingOBE and @Be_redemption, inspirational veterans involved in the Invictus Games which Sage sponsored this year. I love the spirit of the Invictus Games. The triumph of will over adversity strikes a chord with me. You can find out more about this awesome event here.

Gwyneth and Zooey are also interesting to listen to and its amusing to hear Gwyneth talk about KPI’s and business when I’m so used to seeing her onscreen as an actress. She’s clearly into the lingo and passionate about business and I enjoy her and Zooey sharing their stories of entrepreneurship.

After the talks I try to sneak backstage with business vlogger Evan Carmichael to meet the two actresses. A Sage team member that I don’t know shuts us down at the door with a very final sounding ‘no.’ Evan and I smile at each other. As entrepreneurs we both know that it’s hard to stop us when we are determined and the ‘no’ just adds to the pleasure of succeeding. Sure enough, five minutes later I’m having my photo taken with Gwyneth and Zooey, who are both as gorgeous and lovely in real life as I’d imagined. Result!

I’m due on stage in fifteen minutes to give my ‘Looking back from perfect’ talk. I leg it over to the theatre and share the strategy I used to halve my working week and doubled my income in the space of one year. I get a good response from the audience and there are some great questions at the end. I’m extremely grateful to friends that came along to support me. You can see the slides from my talk at

Sage Summit 2016

Afterwards I head upstairs to have lunch with Chairman of Sage, Donald Brydon. He’s a clever man with incredible experience as a FTSE 100 Chairman and excellent knowledge of Sage. I enjoy watching him ask our small group of Sage customers considered questions on what is going well for them with their experience of Sage and what isn’t. It’s so important for all companies to pay attention to what customers love and what they hate about what they do.

After lunch I head to a prep meeting for the panel I’m part of later that day. Together we run through the key questions and the format of the session. Then it’s off to the main hall again to catch the second keynote of the day. Robert Herjavek and Damond John are two hugely successful entrepreneurs who appear on a TV show Shark Tank which is the American format of BBC’s Dragon’s Den. They are thoroughly entertaining with some hilarious banter that makes the series of business nuggets they share all the more enjoyable. Robert is getting married on Sunday. If only I’d known I could have done hime a good deal on wedding invites with our wedding stationery business Ivy Ellen. Afterwards Evan and I blag our way backstage again for a meet and greet with photos. We’re getting to be a dab hands at this now.

I spend the next hour walking the theatres taking photos of talks and sharing them with my Twitter followers to support the different speakers at Sage Summit. I stop for a minute to put some charge into my phone in the meeting area a member of the Sage PR team invites me to join Stephen Kelly and Evan Carmichael on their live Google Hangout. I jump in and the session is a laugh as we share some of our business approaches with those watching online and asking us questions. Stephen and Evan do blabs and hangouts like this fairly regularly so make sure you follow them on Twitter to keep up to date.

I realise I’m running late for my Business without Borders panel session so I make my excuses and hotfoot it to theatre 3. I arrive just in time to join the stage with UK owner of Superfood Market Gemma Price, Adrian Nyland from Carmanah Technologies Corp and Pierce Content Marketing founder Roger Pierce. The session is led by Connie Certusi from Sage. It’s a distinguished panel with a variety of insights into exporting. I scribble a few notes down for myself after hearing the other panellists sharing their thoughts and experiences. See previous talks and slides I’ve done with UKTI on my blog here.

Sage Summit 2016

After our session Connie hooks us up with VIP passes to the Killers gig put on by Sage that evening. I jump on a bus and head back to my hotel to change before heading out to the concert. I’m hungry, but there’s no time to eat and besides I effectively only have $3 left which is not going to get me much. Traffic that evening is a nightmare as roads are blocked off in preparation for Lollapalooza this weekend and AC Milan are playing Bayern Munich at Soldier Field nearby. We get to the gig and things get even more exciting when Stephen Kelly surprises us with backstage passes. It’s going to be an incredible night.

We’re like a group of excited school kids as we get ushered backstage to meet the band before they go on. Next thing you know we are upstairs on a platform looking down on the stage and the crowd below as the Killers begin to play. Having seen lucky people at Glastonbury view gigs like this I’ve always wondered what it would be like. It’s really exciting and a unique angle on the action. After a while I notice another platform on the other side of the stage and decide to explore.

I work my way through the crowd at the front of the stage who are rocking out and having a cracking time. The concert looks and sounds great from all angles. I bump into branding guru Sasha Strauss as I climb the stairs to the second backstage viewing platform. We get to the top and discover that this is where the party is really at. The fans here are mad for the Killers and we rock out with Stephen and his family who are dancing like crazy and bouncing back and forth across the deck. Justin Packshaw and some of the Invictus Games crew are there too. It’s a blast and definitely one of the highlights of my entire trip to Chicago.

Afterwards we head over to a bar called the Public House and Sasha kindly spends time offering me branding tips. I’m a big fan and he clearly loves teaching. I lap it up and make notes of things I can do with our business. Stephen also spends some time discussing Blue Eyed Sun with me and we come up with some great PR ideas that I note to sort when I get back to the UK.

It’s been an amazing day and I’m on cloud nine as I walk home to my hotel through the streets of Chicago. It’s late and as I cross a bridge I’m approached by three men who look like proper gangsters. One of them asks me if I like hiphop and want to rap with him in exchange for money. I explain that I only have $8 left to get me to the airport and decline his offer despite my love of rap music. I think my British accent throws them. We shake hands and I take off towards my hotel pondering how close I came to being mugged and whether I should have given over the last of my cash for the experience of a rap session with DMoss.

I get to bed by 3am and again wonder why on earth I agreed to meet Stephen and Justin for another early morning run in three hours’ time.

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