45 Days — Chapter 3— Open Heart Surgery

“45 Days” is a non-fiction account of my experience as the Founder of Rude Media between May 1, 2016 and June 15, 2016. 45 Days was written starting on June 16th, initially as a therapeutic effort to process my experiences internally, as well as to try to distill down an experience that very few Founders have shared openly.

June 19th, 2016 — I’m sitting in Central Park enjoying one of my favorite past-times: people-watching (again). Olivia & I have been running around New York City for the previous two days, and today we decided to take it easy. A little sunbathing (for her, not me — I can’t support the sun), and an opportunity to reflect on the past, present & future.

Hindsight is 20/20. It’s all too easy to make ‘what if I had…’ scenarios about decisions past. I try not to dwell on it, and instead try to harness those lessons learned and turn them into “next time I’ll…” — because the reality is that our ability to see the flaws in our choices is a direct product of having made them, and without making the wrong decision, it’s often impossible to identify the right one. Founder life more often than not is the school of hard knocks. And more often than not, life knocks hard.

The hardest part of a crisis for a founder is that you must live two parallel existences: the best-case scenario and the worst-case scenario. This is only slightly different from the every day entrepreneurial life; however, as an entrepreneur, you get used to convincing yourself that you are the exception to the statistical failure that is startups. Once failure is actually in view, convincing yourself otherwise is counterproductive, and you really need to kick into gear a dual existence.

Chapter 3: Open Heart Surgery

The first Monday of May — When a ship is taking on water, the captain has three core responsibilities: (1) keep people calm during evacuation, (2) stop the water from coming in, and (3) get the water that’s on the ship off the ship. For a founder, that means (1) keeping the team motivated, (2) getting rid of whatever is causing the company to sink, and (3) figuring out how to use the remaining resources to keep the company alive. Over the weekend I sent out a #general message to @everyone on Slack telling them to be in the office at 9AM Monday morning for breakfast. This was pretty exceptional for Rude Media — weekly standups were scheduled around 10–11AM — I’m not a morning person, nor a 9–5 type of boss. I always measured work based on monthly & quarterly goals, though I always knew how to put the fear of God into my team if I saw that we were getting off track.

I had always strived to be as brutally honest with my team as I was with myself, as I was with our readers. The founder of a startup I’d some work for in the past hadn’t always been 100% on the level with the team — the team knew, and I saw how it affected morale. I didn’t ever want that.

The method has its ups and downs. On the one hand, everyone’s motivation generally followed my mood — if I thought we could conquer the world, so did they. And generally speaking, we could.

On the other hand, sometimes I could be a bit intimidating, because I had no filter. We had hired an intern in the beginning of the year, and on her 5th day or so, she came in sick with a scarf wrapped around her like a neck brace. I let my most senior team members take the lead in the morning, checking in to see if she was OK and letting her know she could take it easy today if she needed, and around noon I checked in with her:

“You know, if you’re not feeling well, you can go home for the day. I’d rather you get better now than be worse off next week.”

She glanced to a colleague, as if for permission.

“Don’t mind Liam. He can be abrasive, but he really doesn’t care if you go home. It’s not a test.”

The team didn’t know exactly what Monday’s breakfast meeting would be about, but they knew that it was directly related to the ambiguity left after last Friday’s surprise cashflow announcement. As we waited for people to poor in between 9:00AM and 9:30AM — strikes, or communication issues, I never really expected the meeting to start at 9 — I encouraged everyone to grab a croissant and a coffee and just shoot the shit. Finally, once 9 out of 10 of us were there (someone had a meeting that morning, or so they told me — I think they were lining up interviews already), I kicked things off.

“Last Friday was tough, I know. If it hit you as hard as it hit me, I’m sure you all have plenty of questions, so let me reiterate: we are not giving up, and until there are zero possibilities for success, we will keep doing everything we can as great as we can. We have a conference at the end of the month that is already profitable, so any last-minute deals are money in the bank. We have three events coming up September & October, of which two of them will be among our biggest budgeted events. Big budgets means big bucks, so we’re going to get ahead of these events this month. The product is still growing, and we have a great brand as perceived from the public, so we’re going to leverage that and start talking to other media companies about either a majority-stake investment or an acquisition.”

I needed everyone to get pumped so that I knew that, no matter what happened, we’d look as good as possible for whoever was looking at us — clients, buyers, investors, those to whom we owed money — and by the end of that breakfast meeting, motivation was as high as could be during crisis mode. Everyone knew what they had to do, and that they had to give it their all — just as I had asked them to do for the last two months, when we were trying to look good for investors.

Fresh off of that meeting, I had already lined up a meeting with one of France’s bigger media companies — a 100% French player that I thought I could get excited about our international & digital expertise. I sat down with their Chief Digital Officer & Director of Corporate Development, and I began the same pitch I had been using for investors for the past few months, only the last slide’s call to action changed from ‘invest’ to ‘acquire.’ Our deck pushed Disclose as the forefront of our business — I had always strived to downplay the media part of our business, despite the fact that it was geared to be a €1 Million+ revenue, profitable business line for us in 2016 (it was profitable every year since our founding in 2013); however, as the conversation continued, I realized that they were more impressed by our events & media activity than they were about our product.

The CDO understood the problems their editorial team faced, and ‘big data’ ‘productivity’ and ‘scalable’ were all words that lit up his eyes, but, if the product was a bit too early stage for seed VCs, it was 100x more early stage for a traditional media company to make a bet. They were willing to run a pilot — to get an an entire section of the editorial team using Disclose, and see how it went from there — which would’ve been great for us if we were funded and looking to built out the team-working side of the product; however, a pilot wouldn’t do us much good if we went under.

The conversation continued, unexpectedly, onto the events side of our business, and I realized that they were particularly interested in how we bootstrapped our events business to 25,000 annual attendees & 100s of partners from 50 countries — I talked about how we had built our events business as a mirror of our editorial line, which means that editorial (that’s me) manages sales, and sales doesn’t dictate editorial. This strategy had cost us financially in the past: I had written a scathing article about a startup studio just weeks after they signed up to be a big exhibitor at our recruitment fair, and they, of course, pulled out, to my sales manager’s dismay. When he told m, I shrugged my shoulders and said “What would you have rather I do? Not say what I think?” He shrugged his shoulders, and I send him the next few inbound requests that came my way to make up for the lost commission.

That’s how things have always been at Rude Media, and it’s how we’ve been able to get international attendees, journalists & partners excited about our events. We don’t pull our punches, and we always set high editorial standards for speakers: we refuse French corporate speaker proposals time & time again because the speaker is their ‘local’ guy, and not on the executive board. Most events seek to have company names to show off — we would rather have the CEO of a small, sexy company than the French marketing manager of a multinational company. It sounds obvious, but take a look at the next conference you’re attending and see how they balance ‘the next big thing’ speakers with ‘the current big thing.’

“Invest in us and we’ll invest in you.”

That’s our motto, and it applies to attendees, journalists, sponsors & speakers: we keep track of everyone who cancels last-minute, or who signs up for a press pass when they‘re an investor or PR person. We also notice people who pay it forward: we give out free tickets because, without any expectations to do so, certain people encourage others to come to our event after they attend.

There’s only one way to grow an event: everyone who came to the previous edition needs to come again the following year. And if they can, they need to come bigger. With Connected Conference, we went from 350 attendees from 10 countries to 1,000 attendees from 25 countries in one year, and we were on our way to 2,500 attendees from 50 countries at the end of May.

At the end of the meeting, I knew two things: (1) we were exceptionally good at organizing events, and (2) the road to acquisition by a traditional French media company was not clear. Still, I was pumped, and our team was pumped. The sales team had set an ambitious monthly goal that they felt they could hit — or at least, they knew they had to — and I was meeting with as many people as I could to get things in motion.

The problem is, I had gotten so caught up in my job of keeping morale high & figuring out a path to success, that I forgot the third part of a captain’s job: dumping excess weight. After the breakfast meeting came the end of day meeting with the Disclose team, and it wasn’t going to be a good one. I had spun it every way I could — so had our CTO — and it was clear that every avenue to success involved laying off the entire product team. Even our CTO.

The product team had spent the day answering user questions, pushing new features, and planning out our May roadmap. When I walked in, they were looking to have a monthly team meeting and figure out how to make the next six weeks count. I pulled the rug out from under them, and didn’t even realize it until the words came out of my mouth — that’s part of the problem of having no filter.

Some of them saw it coming — then again, they would all follow me off a cliff if I told them it’d help the company succeed — but they were all confused as to why I even bothered pumping them up in the morning if I was going to lay them off in the evening. At the time, I didn’t have the heart to tell them that it was because I had held onto hope in the morning that, during the day, a path to success that involved keeping the product team around would present itself. The meeting with the potential acquirer slammed me back down to the reality that, where we were an exciting Media play, we weren’t a compelling enough Product play to be able to make something happen in 45 Days.

Running those meetings back-to-back in that order was draining for me, unfair to them, and it ultimately nullified all the morale-boosting I had done that morning.

I was trying to put out fires while building a log cabin at the same time, and I was getting sloppy. You can’t get sloppy with open heart surgery. If you do, people die. In this case, I was trying to repair the heart of our startup, and I was coming dangerously close to knicking an artery. One false step, and everything would fall apart, and then I’d really be out of options.

To continue reading 45 Days, feel free to click through the Table of Contents below, or subscribe to my posts on Medium — I’ll be adding new chapters regularly.

• Chapter 1: The Last Meeting in April
• Chapter 2: The Seven Stages of Grief
• Chapter 3: Open Heart Surgery
• Chapter 4: It’s easy to Fire in France
• Chapter 5: Ephemeral. Exclusive. Entertaining.
• More Chapters published soon — Subscribe for updates!